Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions

Ting Ma, Xiao Fu, Choonwee Kee, Lili Zong, Yuanhang Pan, Kuo-Wei Huang, Choonhong Tan

Research output: Contribution to journalArticlepeer-review

103 Scopus citations

Abstract

A new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β- unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications of this methodology. Phosphoglycine ester analogues can also be utilized as the Michael donor, affording enantioenriched α-aminophosphonic acid derivatives and phosphonic analogues of (S)-proline. © 2011 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)2828-2831
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number9
DOIs
StatePublished - Mar 9 2011

ASJC Scopus subject areas

  • Biochemistry
  • Colloid and Surface Chemistry
  • Chemistry(all)
  • Catalysis

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