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

6 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 publicationComprehensive Chirality
PublisherElsevier Ltd
Pages328-342
Number of pages15
Volume4
ISBN (Print)9780080951683
DOIs
Publication statusPublished - Sep 1 2012

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Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Suga, S., & Kitamura, M. (2012). 4.17 Asymmetric 1,2-Addition of Organometallics to Carbonyl and Imine Groups. In Comprehensive Chirality (Vol. 4, pp. 328-342). Elsevier Ltd. https://doi.org/10.1016/B978-0-08-095167-6.00416-X