Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols

R. Noyori, S. Suga, K. Kawai, S. Okada, M. Kitamura, N. Oguni, M. Hayashi, T. Kaneko, Y. Matsuda

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216 Citations (Scopus)

Abstract

Nucleophilic addition of dialkylzincs to aldehydes in hydrocarbon solvents is markedly accelerated by the presence of a catalytic amount of a β-dialkylamino alcohol. Use of certain sterically constrained chiral amino alcohols such as 3-exo-(dimethylamino)isoborneol or 1-t-butyl-2-piperidinoethanol effects highly enantioselective catalysis giving secondary alcohols in up to 99% ee. Dimethyl-, diethyl-, di-n-butyl-, and di-n-pentyl-zincs have been employed for the alkylation of substituted benzaldehydes and some olefinic or aliphatic aldehydes. Configurational correlation between the chiral auxiliary and alkylation products is discussed.

Original languageEnglish
Pages (from-to)19-37
Number of pages19
JournalJournal of Organometallic Chemistry
Volume382
Issue number1-2
DOIs
Publication statusPublished - Feb 6 1990
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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    Noyori, R., Suga, S., Kawai, K., Okada, S., Kitamura, M., Oguni, N., Hayashi, M., Kaneko, T., & Matsuda, Y. (1990). Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols. Journal of Organometallic Chemistry, 382(1-2), 19-37. https://doi.org/10.1016/0022-328X(90)85212-H