Gold-catalyzed highly enantioselective synthesis of axially chiral allenes

Vanessa Kar Yan Lo, Man Kin Wong, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

117 Citations (Scopus)

Abstract

Axially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 °C. The reaction has been applied to the synthesis of novel allene-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. A tentative mechanism regarding gold(l)-catalyzed intramolecular hydride transfer was proposed on the basis of deuterium-labeling experiments and ESI-MS analysis of the reaction mixture.
Original languageEnglish
Pages (from-to)517-519
Number of pages3
JournalOrganic Letters
Volume10
Issue number3
DOIs
Publication statusPublished - 7 Feb 2008
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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