Asymmetric Michael reaction of acetaldehyde catalyzed by diphenylprolinol silyl ether

Yujiro Hayashi, Takahiko Itoh, Masahiro Ohkubo, Hayato Ishikawa

Research output: Contribution to journalArticlepeer-review

192 Citations (Scopus)

Abstract

(Chemical Equation Presented) An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS = trimethylsilyl). The desired 1,4-addition products, α-unsubstituted γ-nitro aldehydes, were obtained in good yields with excellent enantioselectivities.

Original languageEnglish
Pages (from-to)4722-4724
Number of pages3
JournalAngewandte Chemie - International Edition
Volume47
Issue number25
DOIs
Publication statusPublished - 2008 Jun 9
Externally publishedYes

Keywords

  • Acetaldehyde
  • Asymmetric catalysis
  • Michael addition
  • Synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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