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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Bibliographic Details
Published inOrganic letters Vol. 26; no. 36; pp. 7546 - 7550
Main Authors Saito, Akira, Shibasaki, Masakatsu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.09.2024
Amer Chemical Soc
Subjects
aldimines
aziridines
catalysts
Chemistry
Chemistry, Organic
Lewis acids
Physical Sciences
Science & Technology
stereoselectivity
FLUORINE
EFFICIENT ACCESS
ENANTIOSELECTIVE SYNTHESIS
ALKYLATION
CONSTRUCTION
AMIDES
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.4c02505

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Summary: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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02505