Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries

Jing Lin, Wing Hong CHAN*, Albert W M LEE, Wai Yeung WONG

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

32 Citations (Scopus)


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
Issue number49
Publication statusPublished - 3 Dec 1999

Scopus Subject Areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

User-Defined Keywords

  • Asymmetric alkylation
  • Chiral suitams
  • Kinetic resolution


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