4.17 Asymmetric 1,2-Addition of Organometallics to Carbonyl and Imine Groups

S. Suga, M. Kitamura

    Research output: Chapter in Book/Report/Conference proceedingChapter

    7 Citations (Scopus)

    Abstract

    The development of asymmetric 1,2-additions of organometallics to carbonyl compounds and imines for the synthesis of chiral alcohols and amines has been overviewed. The highly enantioselective addition reactions of dialkylzincs to aldehydes developed in the mid-1980s have definitely played a key role in this field of chemistry. Hundreds of chiral sources which promote additions of zinc alkyl groups to aldehydes with high enantioselectivities have appeared in the literature, and the chemistry became one of the milestones of asymmetric catalysis in organic synthesis. The subsequent progress in the efficient catalytic asymmetric synthesis of tertiary alcohols by the reactions of ketones and organometallic reagents is also outstanding. Over the past decade, catalytic enantioselective synthesis of chiral amines using asymmetric 1,2-addition of organometallics to imines has become a matter of common knowledge.

    Original languageEnglish
    Title of host publicationSynthetic Methods III - Catalytic Methods
    Subtitle of host publicationC-C Bond Formation
    PublisherElsevier Ltd
    Pages328-342
    Number of pages15
    Volume4
    ISBN (Print)9780080951683
    DOIs
    Publication statusPublished - Sep 2012

    Keywords

    • Aldehyde
    • Chiral alcohol
    • Chiral amine
    • Enantioselective addition
    • Grignard reagent
    • Imine
    • Ketone
    • Organolithium
    • Organomagnesium
    • Organozinc

    ASJC Scopus subject areas

    • Chemistry(all)

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