Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries

Jing Lin, Wing Hong Chan, Albert W.M. Lee, Wai Yeung Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

32 Citations (Scopus)

Abstract

The use of enantiomerically pure sultams (+)-1 and (-)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic α- bromopropanoate or α-bromobutanoate, the enolates of the corresponding N- acyl sultam underwent highly diastereoselective alkylations to afford products with a complete absolute control of two contiguous chiral centres.
Original languageEnglish
Pages (from-to)13983-13998
Number of pages16
JournalTetrahedron
Volume55
Issue number49
DOIs
Publication statusPublished - 3 Dec 1999
Externally publishedYes

Keywords

  • Asymmetric alkylation
  • Chiral suitams
  • Kinetic resolution

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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