Diphenylprolinol silyl ether as a catalyst in an enantioselective, catalytic, tandem Michael/Henry reaction for the control of four stereocenters

Yujiro Hayashi, Tsubasa Okano, Seiji Aratake, Damien Hazelard

Research output: Contribution to journalArticle

215 Citations (Scopus)

Abstract

(Chemical Equation Presented) A choice of three: The tandem Michael/ Henry reaction of a nitroalkene and pentane-1,5-dial (generated in situ) proceeded efficiently when diphenylprolinol silyl ether was used as an organocatalyst to afford substituted nitrocyclohexanecarbaldehydes with high diastereo- and enantioselectivity (see scheme; TMS: trimethylsilyl). Isomerization under basic or acidic conditions diastereoselectively converts the product into two stereoisomers, without compromising the enantioselectivity.

Original languageEnglish
Pages (from-to)4922-4925
Number of pages4
JournalAngewandte Chemie - International Edition
Volume46
Issue number26
DOIs
Publication statusPublished - 2007
Externally publishedYes

Keywords

  • Domino reactions
  • Henry reactions
  • Michael reactions
  • Organocatalysis
  • Tandem reactions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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