An asymmetric and theoretical approach to the Morita-Baylis-Hillman reaction using vinyl-1,2,4-oxadiazoles as nucleophiles
In this work, we present the first enantioselective Morita-Baylis-Hillman reaction using a vinyl heterocycle as the nucleophilic partner. The reaction between vinyl-1,2,4-oxadiazoles and N -substituted isatins is catalyzed by β-isocupreidine (β-ICD), yielding compounds in up to 95% yield and up to 9...
Saved in:
| Published in | Organic & biomolecular chemistry Vol. 23; no. 24; pp. 5872 - 5881 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
18.06.2025
|
| Subjects | |
| Online Access | Get full text |
| ISSN | 1477-0520 1477-0539 1477-0539 |
| DOI | 10.1039/d5ob00540j |
Cover
| Abstract | In this work, we present the first enantioselective Morita-Baylis-Hillman reaction using a vinyl heterocycle as the nucleophilic partner. The reaction between vinyl-1,2,4-oxadiazoles and
N
-substituted isatins is catalyzed by β-isocupreidine (β-ICD), yielding compounds in up to 95% yield and up to 98 : 2 er. The enantioselectivity of the reaction was investigated through theoretical calculations, which allowed us to identify the factors influencing the enantioselectivity, explain the preference for the formation of the
R
enantiomer, and understand the low or absent enantioselectivity when an isatin containing a nitro group is employed. Moreover, the methodology developed enabled the synthesis of chiral analogues of the natural products phidianidine A and phidianidine B, offering unique opportunities to obtain structurally diverse chiral 1,2,4-oxadiazoles.
We report an enantioselective Morita-Baylis-Hillman reaction using vinyl-1,2,4-oxadiazoles as nucleophiles. Computational studies provided insights into the observed enantioselectivity and helped to identify the factors controlling it. |
|---|---|
| AbstractList | In this work, we present the first enantioselective Morita-Baylis-Hillman reaction using a vinyl heterocycle as the nucleophilic partner. The reaction between vinyl-1,2,4-oxadiazoles and N-substituted isatins is catalyzed by β-isocupreidine (β-ICD), yielding compounds in up to 95% yield and up to 98 : 2 er. The enantioselectivity of the reaction was investigated through theoretical calculations, which allowed us to identify the factors influencing the enantioselectivity, explain the preference for the formation of the R enantiomer, and understand the low or absent enantioselectivity when an isatin containing a nitro group is employed. Moreover, the methodology developed enabled the synthesis of chiral analogues of the natural products phidianidine A and phidianidine B, offering unique opportunities to obtain structurally diverse chiral 1,2,4-oxadiazoles.In this work, we present the first enantioselective Morita-Baylis-Hillman reaction using a vinyl heterocycle as the nucleophilic partner. The reaction between vinyl-1,2,4-oxadiazoles and N-substituted isatins is catalyzed by β-isocupreidine (β-ICD), yielding compounds in up to 95% yield and up to 98 : 2 er. The enantioselectivity of the reaction was investigated through theoretical calculations, which allowed us to identify the factors influencing the enantioselectivity, explain the preference for the formation of the R enantiomer, and understand the low or absent enantioselectivity when an isatin containing a nitro group is employed. Moreover, the methodology developed enabled the synthesis of chiral analogues of the natural products phidianidine A and phidianidine B, offering unique opportunities to obtain structurally diverse chiral 1,2,4-oxadiazoles. In this work, we present the first enantioselective Morita–Baylis–Hillman reaction using a vinyl heterocycle as the nucleophilic partner. The reaction between vinyl-1,2,4-oxadiazoles and N-substituted isatins is catalyzed by β-isocupreidine (β-ICD), yielding compounds in up to 95% yield and up to 98 : 2 er. The enantioselectivity of the reaction was investigated through theoretical calculations, which allowed us to identify the factors influencing the enantioselectivity, explain the preference for the formation of the R enantiomer, and understand the low or absent enantioselectivity when an isatin containing a nitro group is employed. Moreover, the methodology developed enabled the synthesis of chiral analogues of the natural products phidianidine A and phidianidine B, offering unique opportunities to obtain structurally diverse chiral 1,2,4-oxadiazoles. In this work, we present the first enantioselective Morita-Baylis-Hillman reaction using a vinyl heterocycle as the nucleophilic partner. The reaction between vinyl-1,2,4-oxadiazoles and N -substituted isatins is catalyzed by β-isocupreidine (β-ICD), yielding compounds in up to 95% yield and up to 98 : 2 er. The enantioselectivity of the reaction was investigated through theoretical calculations, which allowed us to identify the factors influencing the enantioselectivity, explain the preference for the formation of the R enantiomer, and understand the low or absent enantioselectivity when an isatin containing a nitro group is employed. Moreover, the methodology developed enabled the synthesis of chiral analogues of the natural products phidianidine A and phidianidine B, offering unique opportunities to obtain structurally diverse chiral 1,2,4-oxadiazoles. We report an enantioselective Morita-Baylis-Hillman reaction using vinyl-1,2,4-oxadiazoles as nucleophiles. Computational studies provided insights into the observed enantioselectivity and helped to identify the factors controlling it. In this work, we present the first enantioselective Morita-Baylis-Hillman reaction using a vinyl heterocycle as the nucleophilic partner. The reaction between vinyl-1,2,4-oxadiazoles and -substituted isatins is catalyzed by β-isocupreidine (β-ICD), yielding compounds in up to 95% yield and up to 98 : 2 er. The enantioselectivity of the reaction was investigated through theoretical calculations, which allowed us to identify the factors influencing the enantioselectivity, explain the preference for the formation of the enantiomer, and understand the low or absent enantioselectivity when an isatin containing a nitro group is employed. Moreover, the methodology developed enabled the synthesis of chiral analogues of the natural products phidianidine A and phidianidine B, offering unique opportunities to obtain structurally diverse chiral 1,2,4-oxadiazoles. |
| Author | Cormanich, Rodrigo A Coelho, Fernando Piscelli, Bruno A Chagas, Thaynan A. B Santos, Hugo Lima, Sâmia R Fernandes, Fábio S |
| AuthorAffiliation | University of Campinas Institute of Chemistry Laboratório de Síntese de Produtos Naturais e Fármacos Laboratory of Experimental and Theoretical Organic Chemistry Department of Organic Chemistry |
| AuthorAffiliation_xml | – name: Laboratório de Síntese de Produtos Naturais e Fármacos – name: University of Campinas – name: Department of Organic Chemistry – name: Laboratory of Experimental and Theoretical Organic Chemistry – name: Institute of Chemistry |
| Author_xml | – sequence: 1 givenname: Thaynan A. B surname: Chagas fullname: Chagas, Thaynan A. B – sequence: 2 givenname: Bruno A surname: Piscelli fullname: Piscelli, Bruno A – sequence: 3 givenname: Hugo surname: Santos fullname: Santos, Hugo – sequence: 4 givenname: Sâmia R surname: Lima fullname: Lima, Sâmia R – sequence: 5 givenname: Rodrigo A surname: Cormanich fullname: Cormanich, Rodrigo A – sequence: 6 givenname: Fábio S surname: Fernandes fullname: Fernandes, Fábio S – sequence: 7 givenname: Fernando surname: Coelho fullname: Coelho, Fernando |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/40454433$$D View this record in MEDLINE/PubMed |
| BookMark | eNpd0ctPGzEQB2CrAhUIvfQOssSlqtjWzzU-8iq0AnFpz6uJ19s48trB3kVN_nqcBoLEyePRJz_md4B2QgwWoc-UfKOE6--tjFNCpCDzD2ifCqUqIrne2daM7KGDnOeEUK1q8RHtCSKkEJzvo9V5wJCXfW-H5AyG0OJhZmOygzPgMSwWKYKZ4SGu-_g-JjdAdQFL73J167zvIeBkwQwuBjxmF_7iJxeWvqKn7FRU8R-0DlbR21zuwWE03sbFzJX9IdrtwGf76WWdoD8_rn9f3lZ3Dzc_L8_vKsP02VC1tSTKtNS0QmiqzFRxKi2XCsBOmQYFrTjrpCKs45LR2mognWa1qGuulJB8gr5szi1feRxtHpreZWO9h2DjmBvOypw4qRkv9OQdnccxhfK6tdI1F1yzoo5f1DjtbdsskushLZvXqRbwdQNMijkn220JJc06suZKPlz8j-xXwUcbnLLZurdI-TMlX5E6 |
| Cites_doi | 10.1002/jcph.887 10.1002/anie.200462462 10.2174/157019306776819253 10.1039/C5OB00874C 10.2217/nmt-2016-0022 10.1002/chem.200400872 10.1080/00304948.2011.549065 10.1021/ja107858z 10.1002/ajoc.201300093 10.1016/j.ejmech.2020.112418 10.1016/j.dt.2021.12.002 10.1002/anie.201707531 10.1021/acscatal.5b01579 10.1007/s11426-009-0180-2 10.1016/j.tetlet.2018.06.023 10.1021/acs.jmedchem.3c01249 10.1016/S1474-4422(15)00336-1 10.1002/adsc.202001231 10.1016/j.tetlet.2012.11.057 10.1002/anie.200460059 10.1002/ejoc.201200405 10.1021/ol102597s 10.1039/D4RA02369B 10.1039/D3QO01523H 10.1021/acs.joc.2c02765 10.1002/chem.201302665 10.1021/acs.jmedchem.2c01516 10.1021/acscatal.2c06420 10.1016/j.ejmech.2023.115272 10.1039/D3OB00853C 10.1021/ol701547r 10.1039/c3ra41115j 10.3390/molecules15020709 10.1039/c2ra20521a 10.1039/C4OB01358A 10.1021/acs.jmedchem.4c00080 10.1007/s40265-020-01319-7 10.2174/1389557523666230202103719 10.1021/acs.joc.8b02402 10.1016/0040-4039(91)80098-Q 10.1021/acs.joc.2c03073 10.1039/D4MD00113C 10.1021/ja0717865 10.1039/C4RA01492H 10.1021/ol702211d 10.1039/C5OB00182J 10.1002/chem.202202464 10.1016/j.tet.2024.134435 10.1016/j.tet.2017.04.008 10.1039/D4OB01299B 10.1021/ja5111392 10.1021/jo050202j 10.1039/D3QO01047C 10.1021/acs.jmedchem.8b01430 10.1039/C6OB00298F 10.1016/j.tet.2008.02.087 10.1021/jo102094h 10.1039/C1CS15174F 10.1039/C7CP06508F 10.1039/b613741p 10.1021/jo900622x 10.3762/bjoc.12.33 10.1039/c001772h 10.1021/ol3020418 10.1055/s-0037-1612215 10.1021/ja805122j 10.1002/ardp.202200123 10.1021/jm2013248 10.1002/cjoc.201200937 10.1016/j.theochem.2006.04.044 10.1039/c3cc40717a 10.1021/ol047739o 10.1021/acs.orglett.9b01901 10.1021/cr300192h 10.1080/14756366.2022.2115036 10.1039/D3OB00934C 10.1021/acs.orglett.8b02655 10.1021/acs.orglett.3c01082 |
| ContentType | Journal Article |
| Copyright | Copyright Royal Society of Chemistry 2025 |
| Copyright_xml | – notice: Copyright Royal Society of Chemistry 2025 |
| DBID | AAYXX CITATION NPM 7QO 7T7 7TM 8FD C1K FR3 P64 7X8 |
| DOI | 10.1039/d5ob00540j |
| DatabaseName | CrossRef PubMed Biotechnology Research Abstracts Industrial and Applied Microbiology Abstracts (Microbiology A) Nucleic Acids Abstracts Technology Research Database Environmental Sciences and Pollution Management Engineering Research Database Biotechnology and BioEngineering Abstracts MEDLINE - Academic |
| DatabaseTitle | CrossRef PubMed Biotechnology Research Abstracts Technology Research Database Nucleic Acids Abstracts Engineering Research Database Industrial and Applied Microbiology Abstracts (Microbiology A) Biotechnology and BioEngineering Abstracts Environmental Sciences and Pollution Management MEDLINE - Academic |
| DatabaseTitleList | MEDLINE - Academic Biotechnology Research Abstracts CrossRef PubMed |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1477-0539 |
| EndPage | 5881 |
| ExternalDocumentID | 40454433 10_1039_D5OB00540J d5ob00540j |
| Genre | Journal Article |
| GroupedDBID | --- -DZ -~X 0-7 0R~ 123 29N 4.4 705 70~ 7~J AAEMU AAIWI AAJAE AAMEH AANOJ AAWGC AAXHV AAXPP ABASK ABDVN ABEMK ABJNI ABPDG ABRYZ ABXOH ACGFS ACIWK ACLDK ACNCT ACPRK ADMRA ADSRN AEFDR AENEX AENGV AESAV AETIL AFLYV AFOGI AFRAH AFRDS AFRZK AFVBQ AGEGJ AGKEF AGRSR AHGCF AKMSF ALMA_UNASSIGNED_HOLDINGS ALUYA ANUXI APEMP ASKNT AUDPV BLAPV BSQNT C6K CS3 D0L DU5 EBS ECGLT EE0 EF- F5P GGIMP GNO H13 HZ~ H~N IDZ J3I N9A O9- P2P R56 R7B R7C RAOCF RCNCU RNS RPMJG RRA RRC RSCEA SKA SKF SLH TN5 TWZ VH6 WH7 XSW YNT YZZ AAYXX CITATION M4U NPM 7QO 7T7 7TM 8FD C1K FR3 P64 7X8 |
| ID | FETCH-LOGICAL-c298t-d6507cd1cd44917cb7315e357aaeb29a7ad48f5702f35216e9a0f926466377453 |
| ISSN | 1477-0520 1477-0539 |
| IngestDate | Sun Jun 29 02:50:51 EDT 2025 Mon Jun 30 07:24:55 EDT 2025 Fri Jun 20 01:35:25 EDT 2025 Thu Jul 03 08:21:36 EDT 2025 Wed Jun 18 15:20:18 EDT 2025 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 24 |
| Language | English |
| LinkModel | OpenURL |
| MergedId | FETCHMERGED-LOGICAL-c298t-d6507cd1cd44917cb7315e357aaeb29a7ad48f5702f35216e9a0f926466377453 |
| Notes | Electronic supplementary information (ESI) available. CCDC For ESI and crystallographic data in CIF or other electronic format see DOI 2391961 https://doi.org/10.1039/d5ob00540j ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
| ORCID | 0000-0003-0967-2842 0000-0001-8885-8762 0000-0002-7411-5180 0000-0001-7659-1749 0000-0003-1800-1549 0000-0001-8476-8604 |
| PMID | 40454433 |
| PQID | 3219634392 |
| PQPubID | 2047497 |
| PageCount | 1 |
| ParticipantIDs | crossref_primary_10_1039_D5OB00540J pubmed_primary_40454433 proquest_miscellaneous_3214730623 proquest_journals_3219634392 rsc_primary_d5ob00540j |
| PublicationCentury | 2000 |
| PublicationDate | 2025-06-18 |
| PublicationDateYYYYMMDD | 2025-06-18 |
| PublicationDate_xml | – month: 06 year: 2025 text: 2025-06-18 day: 18 |
| PublicationDecade | 2020 |
| PublicationPlace | England |
| PublicationPlace_xml | – name: England – name: Cambridge |
| PublicationTitle | Organic & biomolecular chemistry |
| PublicationTitleAlternate | Org Biomol Chem |
| PublicationYear | 2025 |
| Publisher | Royal Society of Chemistry |
| Publisher_xml | – name: Royal Society of Chemistry |
| References | Sivanandan (D5OB00540J/cit7d/1) 2023; 21 Liang (D5OB00540J/cit9a/1) 2007; 9 Basavaiah (D5OB00540J/cit6b/1) 2012; 41 Reddy (D5OB00540J/cit9c/1) 2018; 59 Nair (D5OB00540J/cit9b/1) 2012; 14 Qian (D5OB00540J/cit18c/1) 2012; 2 Yoshida (D5OB00540J/cit17d/1) 2015; 13 Zhong (D5OB00540J/cit2/1) 2023; 21 Gao (D5OB00540J/cit18e/1) 2015; 5 Wei (D5OB00540J/cit15b/1) 2013; 113 Mansilla (D5OB00540J/cit16/1) 2010; 15 Nakamoto (D5OB00540J/cit24/1) 2013; 19 Nizalapur (D5OB00540J/cit27e/1) 2016; 14 Zhang (D5OB00540J/cit19b/1) 2013; 49 Fabbri (D5OB00540J/cit4a/1) 2016; 6 Hoff (D5OB00540J/cit8c/1) 2022; 28 Wang (D5OB00540J/cit9d/1) 2019 Shi (D5OB00540J/cit17a/1) 2005; 11 Plata (D5OB00540J/cit11e/1) 2015; 137 Zhong (D5OB00540J/cit7b/1) 2011; 43 Bode (D5OB00540J/cit11a/1) 1991; 32 He (D5OB00540J/cit21/1) 2023; 88 Desai (D5OB00540J/cit1b/1) 2022; 355 Tran (D5OB00540J/cit4c/1) 2017; 57 Zhao (D5OB00540J/cit7e/1) 2025; 23 Ayoup (D5OB00540J/cit5c/1) 2023; 252 Xu (D5OB00540J/cit12a/1) 2006; 767 Santos (D5OB00540J/cit10/1) 2023; 13 Pace (D5OB00540J/cit3a/1) 2015 Price (D5OB00540J/cit14a/1) 2005; 70 Pellissier (D5OB00540J/cit15d/1) 2025; 172 Banerjee (D5OB00540J/cit27a/1) 2014; 4 Duan (D5OB00540J/cit19a/1) 2013; 3 Martelli (D5OB00540J/cit25/1) 2012 He (D5OB00540J/cit27d/1) 2018; 20 Fernandes (D5OB00540J/cit22a/1) 2018; 83 Liu (D5OB00540J/cit5e/1) 2024; 67 Basavaiah (D5OB00540J/cit6a/1) 2007; 36 Price (D5OB00540J/cit14b/1) 2005; 7 Abermil (D5OB00540J/cit18a/1) 2008; 130 Fernandes (D5OB00540J/cit23/1) 2020; 201 Zhao (D5OB00540J/cit8e/1) 2023; 25 Robiette (D5OB00540J/cit13b/1) 2007; 129 Kumar (D5OB00540J/cit20b/1) 2015; 13 Mambwe (D5OB00540J/cit5a/1) 2022; 65 Roy (D5OB00540J/cit12c/1) 2009; 74 Uchida (D5OB00540J/cit8a/1) 2019; 21 Lu (D5OB00540J/cit17e/1) 2023; 10 Zhong (D5OB00540J/cit18b/1) 2011; 13 Boström (D5OB00540J/cit1a/1) 2012; 55 Liu (D5OB00540J/cit12d/1) 2017; 19 Ferreira (D5OB00540J/cit4b/1) 2016; 15 Chauhan (D5OB00540J/cit20a/1) 2013; 2 He (D5OB00540J/cit20c/1) 2016; 12 Lamb (D5OB00540J/cit4d/1) 2020; 80 Rambabu (D5OB00540J/cit27b/1) 2013; 54 Liu (D5OB00540J/cit17b/1) 2010; 132 Singh (D5OB00540J/cit7a/1) 2008; 64 Maneesha (D5OB00540J/cit6c/1) 2024; 14 Qian (D5OB00540J/cit5b/1) 2023; 66 Santos (D5OB00540J/cit11b/1) 2004; 43 Wu (D5OB00540J/cit19c/1) 2023; 88 Aggarwal (D5OB00540J/cit13a/1) 2005; 44 Liu (D5OB00540J/cit8b/1) 2021; 363 Zhao (D5OB00540J/cit18d/1) 2014; 12 Buxton (D5OB00540J/cit27c/1) 2017; 56 Pellissier (D5OB00540J/cit15c/1) 2017; 73 Kaye (D5OB00540J/cit7c/1) 2019 Krishna (D5OB00540J/cit15a/1) 2006; 3 Ayoup (D5OB00540J/cit5d/1) 2024; 15 Capretz-Agy (D5OB00540J/cit22b/1) 2020 Zhang (D5OB00540J/cit11c/1) 2009; 52 Burns (D5OB00540J/cit28/1) 2010; 8 Cantillo (D5OB00540J/cit11d/1) 2010; 75 Roy (D5OB00540J/cit12b/1) 2007; 9 Cao (D5OB00540J/cit3b/1) 2022; 18 Liu (D5OB00540J/cit26/1) 2018; 61 Paiva Ferreira (D5OB00540J/cit9e/1) 2023; 23 Wang (D5OB00540J/cit1c/1) 2022; 37 Nam (D5OB00540J/cit8d/1) 2023; 10 Zeng (D5OB00540J/cit17c/1) 2012; 30 |
| References_xml | – issn: 2019 end-page: 101-152 publication-title: Advances in Heterocyclic Chemistry doi: Kaye – issn: 2015 end-page: 85-136 publication-title: Advances in Heterocyclic Chemistry doi: Pace Buscemi Piccionello Pibiri – volume: 57 start-page: 988 issue: 8 year: 2017 ident: D5OB00540J/cit4c/1 publication-title: J. Clin. Pharmacol. doi: 10.1002/jcph.887 – volume: 44 start-page: 1706 issue: 11 year: 2005 ident: D5OB00540J/cit13a/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200462462 – volume: 3 start-page: 137 issue: 2 year: 2006 ident: D5OB00540J/cit15a/1 publication-title: Mini-Rev. Org. Chem. doi: 10.2174/157019306776819253 – volume: 13 start-page: 9022 issue: 34 year: 2015 ident: D5OB00540J/cit17d/1 publication-title: Org. Biomol. Chem. doi: 10.1039/C5OB00874C – volume: 6 start-page: 349 issue: 5 year: 2016 ident: D5OB00540J/cit4a/1 publication-title: Neurodegener. Dis. Manage. doi: 10.2217/nmt-2016-0022 – volume: 11 start-page: 1794 issue: 6 year: 2005 ident: D5OB00540J/cit17a/1 publication-title: Chem. – Eur. J. doi: 10.1002/chem.200400872 – volume: 43 start-page: 1 issue: 1 year: 2011 ident: D5OB00540J/cit7b/1 publication-title: Org. Prep. Proced. Int. doi: 10.1080/00304948.2011.549065 – volume: 132 start-page: 15176 issue: 43 year: 2010 ident: D5OB00540J/cit17b/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja107858z – volume: 2 start-page: 586 issue: 7 year: 2013 ident: D5OB00540J/cit20a/1 publication-title: Asian J. Org. Chem. doi: 10.1002/ajoc.201300093 – volume: 201 start-page: 112418 year: 2020 ident: D5OB00540J/cit23/1 publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2020.112418 – volume: 18 start-page: 344 issue: 3 year: 2022 ident: D5OB00540J/cit3b/1 publication-title: Def. Technol. doi: 10.1016/j.dt.2021.12.002 – volume: 56 start-page: 13824 issue: 44 year: 2017 ident: D5OB00540J/cit27c/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201707531 – volume: 5 start-page: 6608 issue: 11 year: 2015 ident: D5OB00540J/cit18e/1 publication-title: ACS Catal. doi: 10.1021/acscatal.5b01579 – volume: 52 start-page: 1300 year: 2009 ident: D5OB00540J/cit11c/1 publication-title: Sci. China, Ser. B: Chem. doi: 10.1007/s11426-009-0180-2 – volume: 59 start-page: 2859 issue: 30 year: 2018 ident: D5OB00540J/cit9c/1 publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2018.06.023 – volume: 66 start-page: 13891 issue: 20 year: 2023 ident: D5OB00540J/cit5b/1 publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.3c01249 – volume: 15 start-page: 154 issue: 2 year: 2016 ident: D5OB00540J/cit4b/1 publication-title: Lancet Neurol. doi: 10.1016/S1474-4422(15)00336-1 – volume: 363 start-page: 737 issue: 3 year: 2021 ident: D5OB00540J/cit8b/1 publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.202001231 – volume: 54 start-page: 495 issue: 6 year: 2013 ident: D5OB00540J/cit27b/1 publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2012.11.057 – volume: 43 start-page: 4330 issue: 33 year: 2004 ident: D5OB00540J/cit11b/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200460059 – start-page: 4140 year: 2012 ident: D5OB00540J/cit25/1 publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.201200405 – volume: 13 start-page: 82 issue: 1 year: 2011 ident: D5OB00540J/cit18b/1 publication-title: Org. Lett. doi: 10.1021/ol102597s – volume: 14 start-page: 14949 issue: 21 year: 2024 ident: D5OB00540J/cit6c/1 publication-title: RSC Adv. doi: 10.1039/D4RA02369B – volume: 10 start-page: 6153 issue: 24 year: 2023 ident: D5OB00540J/cit8d/1 publication-title: Org. Chem. Front. doi: 10.1039/D3QO01523H – volume: 88 start-page: 6599 issue: 11 year: 2023 ident: D5OB00540J/cit19c/1 publication-title: J. Org. Chem. doi: 10.1021/acs.joc.2c02765 – volume: 19 start-page: 12653 issue: 38 year: 2013 ident: D5OB00540J/cit24/1 publication-title: Chem. – Eur. J. doi: 10.1002/chem.201302665 – volume: 65 start-page: 16695 issue: 24 year: 2022 ident: D5OB00540J/cit5a/1 publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.2c01516 – volume: 13 start-page: 3864 issue: 6 year: 2023 ident: D5OB00540J/cit10/1 publication-title: ACS Catal. doi: 10.1021/acscatal.2c06420 – volume: 252 start-page: 115272 year: 2023 ident: D5OB00540J/cit5c/1 publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2023.115272 – volume: 21 start-page: 6243 year: 2023 ident: D5OB00540J/cit7d/1 publication-title: Org. Biomol. Chem. doi: 10.1039/D3OB00853C – volume: 9 start-page: 4119 issue: 21 year: 2007 ident: D5OB00540J/cit9a/1 publication-title: Org. Lett. doi: 10.1021/ol701547r – volume: 3 start-page: 10127 issue: 26 year: 2013 ident: D5OB00540J/cit19a/1 publication-title: RSC Adv. doi: 10.1039/c3ra41115j – volume: 15 start-page: 709 issue: 2 year: 2010 ident: D5OB00540J/cit16/1 publication-title: Molecules doi: 10.3390/molecules15020709 – volume: 2 start-page: 6042 issue: 14 year: 2012 ident: D5OB00540J/cit18c/1 publication-title: RSC Adv. doi: 10.1039/c2ra20521a – volume: 12 start-page: 8072 issue: 40 year: 2014 ident: D5OB00540J/cit18d/1 publication-title: Org. Biomol. Chem. doi: 10.1039/C4OB01358A – volume: 67 start-page: 10622 issue: 13 year: 2024 ident: D5OB00540J/cit5e/1 publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.4c00080 – volume: 80 start-page: 841 year: 2020 ident: D5OB00540J/cit4d/1 publication-title: Drugs doi: 10.1007/s40265-020-01319-7 – volume: 23 start-page: 1691 issue: 17 year: 2023 ident: D5OB00540J/cit9e/1 publication-title: Mini-Rev. Med. Chem. doi: 10.2174/1389557523666230202103719 – volume: 83 start-page: 15118 issue: 24 year: 2018 ident: D5OB00540J/cit22a/1 publication-title: J. Org. Chem. doi: 10.1021/acs.joc.8b02402 – volume: 32 start-page: 5611 issue: 40 year: 1991 ident: D5OB00540J/cit11a/1 publication-title: Tetrahedron Lett. doi: 10.1016/0040-4039(91)80098-Q – volume: 88 start-page: 3802 issue: 6 year: 2023 ident: D5OB00540J/cit21/1 publication-title: J. Org. Chem. doi: 10.1021/acs.joc.2c03073 – volume: 15 start-page: 2080 issue: 6 year: 2024 ident: D5OB00540J/cit5d/1 publication-title: RSC Med. Chem. doi: 10.1039/D4MD00113C – volume: 129 start-page: 15513 issue: 50 year: 2007 ident: D5OB00540J/cit13b/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0717865 – volume: 4 start-page: 33236 year: 2014 ident: D5OB00540J/cit27a/1 publication-title: RSC Adv. doi: 10.1039/C4RA01492H – volume: 9 start-page: 4873 issue: 23 year: 2007 ident: D5OB00540J/cit12b/1 publication-title: Org. Lett. doi: 10.1021/ol702211d – volume: 13 start-page: 5629 issue: 20 year: 2015 ident: D5OB00540J/cit20b/1 publication-title: Org. Biomol. Chem. doi: 10.1039/C5OB00182J – volume: 28 start-page: e202202464 issue: 63 year: 2022 ident: D5OB00540J/cit8c/1 publication-title: Chem. – Eur. J. doi: 10.1002/chem.202202464 – volume: 172 start-page: 134435 year: 2025 ident: D5OB00540J/cit15d/1 publication-title: Tetrahedron doi: 10.1016/j.tet.2024.134435 – volume: 73 start-page: 2831 issue: 20 year: 2017 ident: D5OB00540J/cit15c/1 publication-title: Tetrahedron doi: 10.1016/j.tet.2017.04.008 – volume: 23 start-page: 1292 year: 2025 ident: D5OB00540J/cit7e/1 publication-title: Org. Biomol. Chem. doi: 10.1039/D4OB01299B – volume: 137 start-page: 3811 issue: 11 year: 2015 ident: D5OB00540J/cit11e/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja5111392 – volume: 70 start-page: 3980 issue: 10 year: 2005 ident: D5OB00540J/cit14a/1 publication-title: J. Org. Chem. doi: 10.1021/jo050202j – volume: 10 start-page: 5076 issue: 20 year: 2023 ident: D5OB00540J/cit17e/1 publication-title: Org. Chem. Front. doi: 10.1039/D3QO01047C – volume: 61 start-page: 11298 issue: 24 year: 2018 ident: D5OB00540J/cit26/1 publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.8b01430 – volume: 14 start-page: 3623 issue: 14 year: 2016 ident: D5OB00540J/cit27e/1 publication-title: Org. Biomol. Chem. doi: 10.1039/C6OB00298F – volume: 64 start-page: 4511 issue: 20 year: 2008 ident: D5OB00540J/cit7a/1 publication-title: Tetrahedron doi: 10.1016/j.tet.2008.02.087 – volume: 75 start-page: 8615 issue: 24 year: 2010 ident: D5OB00540J/cit11d/1 publication-title: J. Org. Chem. doi: 10.1021/jo102094h – volume: 41 start-page: 68 issue: 1 year: 2012 ident: D5OB00540J/cit6b/1 publication-title: Chem. Soc. Rev. doi: 10.1039/C1CS15174F – volume: 19 start-page: 30647 issue: 45 year: 2017 ident: D5OB00540J/cit12d/1 publication-title: Phys. Chem. Chem. Phys. doi: 10.1039/C7CP06508F – start-page: 622 year: 2020 ident: D5OB00540J/cit22b/1 publication-title: Synlett – volume: 36 start-page: 1581 issue: 10 year: 2007 ident: D5OB00540J/cit6a/1 publication-title: Chem. Soc. Rev. doi: 10.1039/b613741p – volume: 74 start-page: 6936 issue: 18 year: 2009 ident: D5OB00540J/cit12c/1 publication-title: J. Org. Chem. doi: 10.1021/jo900622x – volume: 12 start-page: 309 year: 2016 ident: D5OB00540J/cit20c/1 publication-title: Beilstein J. Org. Chem. doi: 10.3762/bjoc.12.33 – volume: 8 start-page: 2777 issue: 12 year: 2010 ident: D5OB00540J/cit28/1 publication-title: Org. Biomol. Chem. doi: 10.1039/c001772h – volume: 14 start-page: 4580 issue: 17 year: 2012 ident: D5OB00540J/cit9b/1 publication-title: Org. Lett. doi: 10.1021/ol3020418 – start-page: 748 year: 2019 ident: D5OB00540J/cit9d/1 publication-title: Synlett doi: 10.1055/s-0037-1612215 – volume: 130 start-page: 12596 issue: 38 year: 2008 ident: D5OB00540J/cit18a/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja805122j – start-page: 85 volume-title: Advances in Heterocyclic Chemistry year: 2015 ident: D5OB00540J/cit3a/1 – volume: 355 start-page: e2200123 issue: 9 year: 2022 ident: D5OB00540J/cit1b/1 publication-title: Arch. Pharm. doi: 10.1002/ardp.202200123 – volume: 55 start-page: 1817 issue: 5 year: 2012 ident: D5OB00540J/cit1a/1 publication-title: J. Med. Chem. doi: 10.1021/jm2013248 – volume: 30 start-page: 2631 issue: 11 year: 2012 ident: D5OB00540J/cit17c/1 publication-title: Chin. J. Chem. doi: 10.1002/cjoc.201200937 – volume: 767 start-page: 61 issue: 1–3 year: 2006 ident: D5OB00540J/cit12a/1 publication-title: J. Mol. Struct.:THEOCHEM doi: 10.1016/j.theochem.2006.04.044 – volume: 49 start-page: 3300 issue: 32 year: 2013 ident: D5OB00540J/cit19b/1 publication-title: Chem. Commun. doi: 10.1039/c3cc40717a – volume: 7 start-page: 147 issue: 1 year: 2005 ident: D5OB00540J/cit14b/1 publication-title: Org. Lett. doi: 10.1021/ol047739o – volume: 21 start-page: 6199 issue: 16 year: 2019 ident: D5OB00540J/cit8a/1 publication-title: Org. Lett. doi: 10.1021/acs.orglett.9b01901 – volume: 113 start-page: 6659 issue: 8 year: 2013 ident: D5OB00540J/cit15b/1 publication-title: Chem. Rev. doi: 10.1021/cr300192h – start-page: 101 volume-title: Advances in Heterocyclic Chemistry year: 2019 ident: D5OB00540J/cit7c/1 – volume: 37 start-page: 2304 issue: 1 year: 2022 ident: D5OB00540J/cit1c/1 publication-title: J. Enzyme Inhib. Med. Chem. doi: 10.1080/14756366.2022.2115036 – volume: 21 start-page: 7511 issue: 37 year: 2023 ident: D5OB00540J/cit2/1 publication-title: Org. Biomol. Chem. doi: 10.1039/D3OB00934C – volume: 20 start-page: 6183 issue: 19 year: 2018 ident: D5OB00540J/cit27d/1 publication-title: Org. Lett. doi: 10.1021/acs.orglett.8b02655 – volume: 25 start-page: 3497 issue: 19 year: 2023 ident: D5OB00540J/cit8e/1 publication-title: Org. Lett. doi: 10.1021/acs.orglett.3c01082 |
| SSID | ssj0019764 |
| Score | 2.4632723 |
| Snippet | In this work, we present the first enantioselective Morita-Baylis-Hillman reaction using a vinyl heterocycle as the nucleophilic partner. The reaction between... In this work, we present the first enantioselective Morita–Baylis–Hillman reaction using a vinyl heterocycle as the nucleophilic partner. The reaction between... |
| SourceID | proquest pubmed crossref rsc |
| SourceType | Aggregation Database Index Database Publisher |
| StartPage | 5872 |
| SubjectTerms | Enantiomers Natural products Nucleophiles Oxadiazoles |
| Title | An asymmetric and theoretical approach to the Morita-Baylis-Hillman reaction using vinyl-1,2,4-oxadiazoles as nucleophiles |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/40454433 https://www.proquest.com/docview/3219634392 https://www.proquest.com/docview/3214730623 |
| Volume | 23 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1db9MwFLVKJ8FeEF-DwEBG8LaZtY7TJI9dGSrTBkjrpL1VtpOMoCap1hbR_g_-L9dfScaGBDw0qpymqXJOb851rs9F6K2IWOInkSTKW4SwQGREgIgjLBmIMAWJzbQT0-mnwficHV8EF53Oz1bV0mop3snNretK_gdVGANc1SrZf0C2_lIYgPeAL2wBYdj-FcbDco8v1kWhumJJVwtZr0t0duFOXp5WaiKAHEKOni_IOJ_N1Pw9iEbTLXylZw2-5-V6RiC8jSi8GKl-KPOCjbJ9Ui1pSmV_XM2_QixZtHWtWdIpNZHUin7XdHdPuoZyrTqCS25rk_i6hF8wbDo_f8kX6klCbllXVs1U65nqdqyPG68uKzd6khda_Z7pB_60yLmtgLQTGTRQBVc29qYm-LIwBM4YcyMXnc1qZMtCylqxNohM058bN4GerzxUk6ASWpB-a38IAJwXmg5MmQ8y48Lxm-W223UHbdEQJFkXbQ2PJh9P6sdToOGY87r144PmVNvorjv4utC5kb2AlrlyPWa0lpk8QPdtEoKHhlEPUSctH6F7IwfVY7QZlrhhFgZm4RazsGMWXlZqHN_KLOyYhTWzsGXWPt2_xio4D26z6gk6_3A0GY2J7dJBJI2jJUlA44cy6cuEMcj9pQj9fpD6Qch5KmjMQ56wKAvCHs1A7PcHacx7WQw6HC4s5B6Bv4O6ZVWmzxBmWS9OpUgGqoG07IeC9wUTEDsiKSEvzjz0xl3S6dyYsUx1EYUfT98Hnw81Bsce2nVXe2r_rIupT9WtBtQ39dDrendhWM3LtFrpzzC44UFC4KGnBqX6NA5VD-0AbPVwg_zzPx7yAm03dN9F3eXVKn0JSnYpXlle_QJ0o566 |
| linkProvider | Royal Society of Chemistry |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=An+asymmetric+and+theoretical+approach+to+the+Morita-Baylis-Hillman+reaction+using+vinyl-1%2C2%2C4-oxadiazoles+as+nucleophiles&rft.jtitle=Organic+%26+biomolecular+chemistry&rft.au=Chagas%2C+Thaynan+A+B&rft.au=Piscelli%2C+Bruno+A&rft.au=Santos%2C+Hugo&rft.au=Lima%2C+S%C3%A2mia+R&rft.date=2025-06-18&rft.eissn=1477-0539&rft.volume=23&rft.issue=24&rft.spage=5872&rft_id=info:doi/10.1039%2Fd5ob00540j&rft_id=info%3Apmid%2F40454433&rft.externalDocID=40454433 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1477-0520&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1477-0520&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1477-0520&client=summon |