Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether

Liansuo Zu, Hao Li, Jian Wang, Xinhong Yu, Wei Wang

Research output: Contribution to journalArticlepeer-review

105 Scopus citations

Abstract

A recyclable and reusable (S) diphenylpyrrolinol silyl ether I organocatalyst bearing a n-C8F17 fluorous tag has been demonstrated for promoting the asymmetric Michael addition reactions of a wide range of aldehydes with both aryl and alkyl-substituted nitroolefins and excellent levels of enantio- and diastereoselectivities are achieved. The catalyst I can be conveniently recovered by fluorous solid-phase extraction and subsequently reused (up to eight cycles) without significant loss of its catalytic activity and stereoselectivity for the process.

Original languageEnglish (US)
Pages (from-to)5131-5134
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number29
DOIs
StatePublished - Jul 17 2006
Externally publishedYes

Keywords

  • Asymmetric organocatalysis
  • Diphenylpyrrolinol silyl ether
  • Fluorous chemistry
  • Michael addition reaction
  • Nitroolefin

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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