On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum

Neelesh A. Kulkarni, Ching Fa Yao, Kwunmin Chen

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.

Original languageEnglish
Pages (from-to)7816-7822
Number of pages7
JournalTetrahedron
Volume63
Issue number33
DOIs
Publication statusPublished - 2007 Aug 13

Keywords

  • Allylation
  • Chiral auxiliary
  • Glyoxylic oxime ether
  • Triallylaluminum

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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