Synthesis of chiral sultams and their application as chiral auxiliaries in an asymmetric Diels-Alder reaction

Hong Kui Zhang, Wing Hong Chan, Albert W.M. Lee, Wai Yeung Wong, Ping Fang Xia

Research output: Journal article publicationJournal articleAcademic researchpeer-review

24 Citations (Scopus)

Abstract

A number of bicyclic chiral sultams were synthesized based on 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrones with prop-1-ene-1,3- sultone. The corresponding N-enoyl sultams were prepared by acylation. Their relative effectiveness as new chiral auxiliaries in asymmetric synthesis was evaluated for the asymmetric Diels-Alder reactions with cyclopentadiene. Good chemical yield and excellent endo selectivity were observed. The relationship between the structure and their effectiveness in promoting asymmetric induction of the synthetic chiral sultams was investigated.
Original languageEnglish
Pages (from-to)761-771
Number of pages11
JournalTetrahedron Asymmetry
Volume16
Issue number4
DOIs
Publication statusPublished - 21 Feb 2005
Externally publishedYes

ASJC Scopus subject areas

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

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