A diarylprolinol in an asymmetric, catalytic, and direct crossed-aldol reaction of acetaldehyde

Yujiro Hayashi, Takahiko Itoh, Seiji Aratake, Hayato Ishikawa

Research output: Contribution to journalArticlepeer-review

167 Citations (Scopus)

Abstract

(Chemical Equation Presented) No over-reacting: A diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of acetaldehyde, affording β-hydroxy α-unsubstituted aldehydes in good yield with excellent enantioselectivity (see scheme). In the proposed transition state the aldehyde reacts on the more hindered face of the intermediate enamine as a consequence of the hydrogen bond between the aldehyde and the OH group of the organocatalyst.

Original languageEnglish
Pages (from-to)2082-2084
Number of pages3
JournalAngewandte Chemie - International Edition
Volume47
Issue number11
DOIs
Publication statusPublished - 2008 Feb 28

Keywords

  • Acetaldehyde
  • Aldol reaction
  • Asymmetric catalysis
  • Organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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