Asymmetric alcoholysis of 2-phenyl-5(4H)-oxazolones by the catalytic mixture of cyclo[(S)-His-(S)-Phe] with chiral auxiliaries

Lunjia Xie, Wenting Hua, Albert S.C. Chan, Yun Chung Leung

Research output: Journal article publicationJournal articleAcademic researchpeer-review

40 Citations (Scopus)

Abstract

Some derivatives of dipeptides containing a His residue catalyzed the ring opening of 2-phenyl-4-benzyl-5(4H)-oxazolone by methanol. The mixture of cyclo[(S)-His-(S)-Phe] (CHP) with chiral auxiliaries which possess both a hydrogen-bond donor and a hydrogen-bond acceptor was a more effective and enantioselective catalyst than the CHP alone. The influence of racemic and the two enantiomerically pure auxiliaries on the cyclo[(S)-His-(S)-Phe]- catalyzed alcoholysis of the 5(4H)-oxazolone was different. A mixture of CHP with L-diisopropyl tartrate catalyzed the enantioselective ring opening of 2- phenyl-4-benzyl-5(4H)-oxazolone by methanol, ethanol and n-butanol, preferentially affording the N-benzoyl-L-phenylalaninates (20-39% e.e.). (C) 2000 Elsevier Science Ltd.
Original languageEnglish
Pages (from-to)4715-4728
Number of pages14
JournalTetrahedron Asymmetry
Volume10
Issue number24
DOIs
Publication statusPublished - 17 Dec 1999

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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