Organocatalyst-mediated dehydrogenation of aldehydes to α,β-unsaturated aldehydes, and oxidative and enantioselective reaction of aldehydes and nitromethane catalyzed by diphenylprolinol silyl ether

Yujiro Hayashi, Takahiko Itoh, Hayato Ishikawa

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

A one-pot transformation of aldehydes into α,β-unsaturated aldehydes was developed using both N-benzyl-N-methylamine and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as catalysts and MnO2 as a terminal oxidant. An oxidative and enantioselective reaction of aldehydes and nitromethane was established using both diphenylprolinol silyl ether and DDQ as a catalyst with MnO2 as a terminal oxidant, in which synthetically important β-substituted γ-nitro aldehydes were obtained with excellent enantioselectivity.

Original languageEnglish
Pages (from-to)3661-3669
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume355
Issue number18
DOIs
Publication statusPublished - 2013 Dec 16

Keywords

  • asymmetric reaction
  • one-pot reaction
  • organocatalysis
  • oxidative reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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