Catalytic Asymmetric Mannich-Type Reaction of α‑Haloacetonitriles
An asymmetric Mannich-type addition of aldimines and haloacetonitriles is reported here, yielding halogenated aminonitriles with excellent stereoselectivity, facilitated by a pincer Ni(II) complex as a catalyst. Haloacetonitriles are recognized as reactive electrophiles, and the possibility of thei...
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| Published in | Organic letters Vol. 26; no. 36; pp. 7546 - 7550 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
13.09.2024
Amer Chemical Soc |
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| Online Access | Get full text |
| ISSN | 1523-7060 1523-7052 1523-7052 |
| DOI | 10.1021/acs.orglett.4c02505 |
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| Abstract | An asymmetric Mannich-type addition of aldimines and haloacetonitriles is reported here, yielding halogenated aminonitriles with excellent stereoselectivity, facilitated by a pincer Ni(II) complex as a catalyst. Haloacetonitriles are recognized as reactive electrophiles, and the possibility of their use as a pronucleophile has been almost neglected for many years. The resulting adduct can be readily converted into various valuable derivatives, including chiral aziridines, starting from chlorinated compounds. |
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| AbstractList | An asymmetric Mannich-type addition of aldimines and haloacetonitriles is reported here, yielding halogenated aminonitriles with excellent stereoselectivity, facilitated by a pincer Ni(II) complex as a catalyst. Haloacetonitriles are recognized as reactive electrophiles, and the possibility of their use as a pronucleophile has been almost neglected for many years. The resulting adduct can be readily converted into various valuable derivatives, including chiral aziridines, starting from chlorinated compounds. An asymmetric Mannich-type addition of aldimines and haloacetonitriles is reported here, yielding halogenated aminonitriles with excellent stereoselectivity, facilitated by a pincer Ni(II) complex as a catalyst. Haloacetonitriles are recognized as reactive electrophiles, and the possibility of their use as a pronucleophile has been almost neglected for many years. The resulting adduct can be readily converted into various valuable derivatives, including chiral aziridines, starting from chlorinated compounds. An asymmetric Mannich-type addition of aldimines and haloacetonitriles is reported here, yielding halogenated aminonitriles with excellent stereoselectivity, facilitated by a pincer Ni(II) complex as a catalyst. Haloacetonitriles are recognized as reactive electrophiles, and the possibility of their use as a pronucleophile has been almost neglected for many years. The resulting adduct can be readily converted into various valuable derivatives, including chiral aziridines, starting from chlorinated compounds.An asymmetric Mannich-type addition of aldimines and haloacetonitriles is reported here, yielding halogenated aminonitriles with excellent stereoselectivity, facilitated by a pincer Ni(II) complex as a catalyst. Haloacetonitriles are recognized as reactive electrophiles, and the possibility of their use as a pronucleophile has been almost neglected for many years. The resulting adduct can be readily converted into various valuable derivatives, including chiral aziridines, starting from chlorinated compounds. |
| Author | Shibasaki, Masakatsu Saito, Akira |
| AuthorAffiliation | Institute of Microbial Chemistry (BIKAKEN) |
| AuthorAffiliation_xml | – name: Institute of Microbial Chemistry (BIKAKEN) |
| Author_xml | – sequence: 1 givenname: Akira surname: Saito fullname: Saito, Akira – sequence: 2 givenname: Masakatsu orcidid: 0000-0001-8862-582X surname: Shibasaki fullname: Shibasaki, Masakatsu email: mshibasa@bikaken.or.jp |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/39230954$$D View this record in MEDLINE/PubMed |
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| Keywords | FLUORINE EFFICIENT ACCESS ENANTIOSELECTIVE SYNTHESIS ALKYLATION CONSTRUCTION AMIDES |
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| Snippet | An asymmetric Mannich-type addition of aldimines and haloacetonitriles is reported here, yielding halogenated aminonitriles with excellent stereoselectivity,... |
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| SubjectTerms | aldimines aziridines catalysts Chemistry Chemistry, Organic Lewis acids Physical Sciences Science & Technology stereoselectivity |
| Title | Catalytic Asymmetric Mannich-Type Reaction of α‑Haloacetonitriles |
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