KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of N‑Sulfinylimines Using HFC-125
A protocol for the stereodivergent pentafluoroethylation of N-sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allo...
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| Published in | Journal of organic chemistry Vol. 87; no. 23; pp. 15806 - 15819 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
02.12.2022
American Chemical Society (ACS) Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-3263 1520-6904 1520-6904 |
| DOI | 10.1021/acs.joc.2c01821 |
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| Abstract | A protocol for the stereodivergent pentafluoroethylation of N-sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allows the KHMDS/triglyme cryptate to be a straightforward and cheap alternative to previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P4- t Bu. |
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| AbstractList | A protocol for the stereodivergent pentafluoroethylation of
-sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allows the KHMDS/triglyme cryptate to be a straightforward and cheap alternative to previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P
-
Bu. A protocol for the stereodivergent pentafluoroethylation of N-sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allows the KHMDS/triglyme cryptate to be a straightforward and cheap alternative to previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P4-tBu. A protocol for the stereodivergent pentafluoroethylation of N-sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allows the KHMDS/triglyme cryptate to be a straightforward and cheap alternative to previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P4-tBu.A protocol for the stereodivergent pentafluoroethylation of N-sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allows the KHMDS/triglyme cryptate to be a straightforward and cheap alternative to previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P4-tBu. A protocol for the stereodivergent pentafluoroethylation of N-sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allows the KHMDS/triglyme cryptate to be a straightforward and cheap alternative to previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P4- t Bu. |
| Author | Iwasaki, Hiroto Mahmoud, Elsayed M. Shibata, Norio Fujihira, Yamato Cahard, Dominique Sumii, Yuji Kagawa, Takumi Adachi, Hiroaki |
| AuthorAffiliation | CNRS UMR 6014 COBRA, Normandie Université Department of Nanopharmaceutical Sciences Zagazig University Department of Life Science and Applied Chemistry Nagoya Institute of Technology Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy |
| AuthorAffiliation_xml | – name: Zagazig University – name: Department of Life Science and Applied Chemistry – name: Department of Nanopharmaceutical Sciences – name: CNRS UMR 6014 COBRA, Normandie Université – name: Nagoya Institute of Technology – name: Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy |
| Author_xml | – sequence: 1 givenname: Yuji orcidid: 0000-0003-3900-1089 surname: Sumii fullname: Sumii, Yuji organization: Nagoya Institute of Technology – sequence: 2 givenname: Hiroto surname: Iwasaki fullname: Iwasaki, Hiroto organization: Nagoya Institute of Technology – sequence: 3 givenname: Yamato surname: Fujihira fullname: Fujihira, Yamato organization: Nagoya Institute of Technology – sequence: 4 givenname: Elsayed M. surname: Mahmoud fullname: Mahmoud, Elsayed M. organization: Zagazig University – sequence: 5 givenname: Hiroaki surname: Adachi fullname: Adachi, Hiroaki – sequence: 6 givenname: Takumi surname: Kagawa fullname: Kagawa, Takumi – sequence: 7 givenname: Dominique orcidid: 0000-0002-8510-1315 surname: Cahard fullname: Cahard, Dominique organization: CNRS UMR 6014 COBRA, Normandie Université – sequence: 8 givenname: Norio orcidid: 0000-0002-3742-4064 surname: Shibata fullname: Shibata, Norio email: nozshiba@nitech.ac.jp organization: Nagoya Institute of Technology |
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| CitedBy_id | crossref_primary_10_1002_tcr_202300029 crossref_primary_10_1002_tcr_202300117 crossref_primary_10_1016_j_jfluchem_2023_110092 crossref_primary_10_1021_acs_orglett_4c03274 crossref_primary_10_1016_j_jfluchem_2024_110349 crossref_primary_10_1002_tcr_202200262 |
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| Contributor | Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie) Zagazig University Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA) ; Institut de Chimie Organique Fine (IRCOF) ; Université de Rouen Normandie (UNIROUEN) ; Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie) ; Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN) ; Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie) ; Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Molé |
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| Snippet | A protocol for the stereodivergent pentafluoroethylation of N-sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the... A protocol for the stereodivergent pentafluoroethylation of -sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the... |
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| SubjectTerms | [CHIM.ORGA]Chemical Sciences/Organic chemistry Chemical Sciences Chemistry Chemistry, Organic Crown Ethers Fluorocarbons Organic chemistry Physical Sciences Polyethylene Glycols Science & Technology |
| Title | KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of N‑Sulfinylimines Using HFC-125 |
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