Asymmetric diels-alder reactions of α,β-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether salt in the presence of water

Yujiro Hayashi, Sampak Samanta, Hiroaki Gotoh, Hayato Ishikawa

Research output: Contribution to journalArticlepeer-review

135 Citations (Scopus)

Abstract

(Chemical Equation Presented) Water, water, everywhere: The title reaction predominantly affords the exo isomer with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). The synthesis can be carried out without organic solvents and provides the products by distillation. Water increases the rate and enantioselectivity of the reaction.

Original languageEnglish
Pages (from-to)6634-6637
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number35
DOIs
Publication statusPublished - 2008 Aug 18
Externally publishedYes

Keywords

  • Asymmetric synthesis
  • Cycloaddition
  • Enantioselectivity
  • Organocatalysis
  • Water chemistry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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