Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes

Yujiro Hayashi, Hiroaki Gotoh, Takaaki Hayashi, Mitsuru Shoji

Research output: Contribution to journalArticle

961 Citations (Scopus)

Abstract

(Chemical Equation Presented) The direct, catalytic, asymmetric Michael addition of aldehydes to nitroolefins in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme). The desired 1,4-addition products were obtained in nearly optically pure form in good yield with high syn diastereoselectivity. TMS = trimethylsilyl.

Original languageEnglish
Pages (from-to)4212-4215
Number of pages4
JournalAngewandte Chemie - International Edition
Volume44
Issue number27
DOIs
Publication statusPublished - 2005 Jul 4
Externally publishedYes

Fingerprint

Aldehydes
Ethers
diphenylprolinol silyl ether

Keywords

  • Asymmetric catalysis
  • Diphenylprolinol
  • Michael addition
  • Nitroalkenes
  • Organocatalysis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes. / Hayashi, Yujiro; Gotoh, Hiroaki; Hayashi, Takaaki; Shoji, Mitsuru.

In: Angewandte Chemie - International Edition, Vol. 44, No. 27, 04.07.2005, p. 4212-4215.

Research output: Contribution to journalArticle

Hayashi, Yujiro ; Gotoh, Hiroaki ; Hayashi, Takaaki ; Shoji, Mitsuru. / Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes. In: Angewandte Chemie - International Edition. 2005 ; Vol. 44, No. 27. pp. 4212-4215.
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