Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary: Efficient synthesis of highly optically active two stereoisomers

Jung Hsuan Chen, Uppala Venkatesham, Li Chen Lee, Kwunmin Chen

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18 Citations (Scopus)

Abstract

Complementary allylation conditions were developed for the synthesis of both diastereomers of tertiary homoallylic alcohols. Treatment of camphor N-tosylpyrazolidinone derived α-ketoamides with allyltributylstannane afforded both the individual homoallylic alcohols in high optical purity (up to 98% de) when the reaction was carried out in the presence of Sn(OTf)2 and PdCl2, respectively. The stereochemical outcome and reversal of stereoselectivity in the reaction are proposed based on 13C NMR and FTIR studies.

Original languageEnglish
Pages (from-to)887-893
Number of pages7
JournalTetrahedron
Volume62
Issue number5
DOIs
Publication statusPublished - 2006 Jan 30

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Keywords

  • Allylation
  • Chiral auxiliary
  • Reversal of stereoselectivity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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