Oxidative and enantioselective cross-coupling of aldehydes and nitromethane catalyzed by diphenylprolinol silyl ether

Yujiro Hayashi, Takahiko Itoh, Hayato Ishikawa

Research output: Contribution to journalArticlepeer-review

111 Citations (Scopus)

Abstract

Synthetically important β-substituted γ-nitro aldehydes have been synthesized with excellent enantioselectivity by the cross-coupling reaction of β-aryl substituted aldehydes or Y γ-unsaturated aldehydes and nitromethane using 2,3-dichloro-5,6-dicyanoquinone (DDQ) and diphenylprolinol silyl ether as an oxidant and catalyst, respectively (see scheme; TMS=trimethylsilyl).

Original languageEnglish
Pages (from-to)3920-3924
Number of pages5
JournalAngewandte Chemie - International Edition
Volume50
Issue number17
DOIs
Publication statusPublished - 2011 Apr 18
Externally publishedYes

Keywords

  • asymmetric catalysis
  • cross-coupling
  • one-pot reaction
  • organocatalysis
  • oxidative reaction

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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