Diastereoselective oxidation of substituted thietanes and stereoselective oxidation of their sulfoxides

Richard S. Glass, Waheguru Pal Singh, Bruce A. Hay

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

Oxidation of substituted thietanes 1a, b, and 6 with m-chloroperoxybenzoic acid preferentially gives the corresponding cis-sulfoxides with modest diastereoselectivity. Selective oxidation of the trans over the cis diastereomeric pairs of sulfoxides 2a, 3a; 2b, 3b; 7, 8 occurs with moderate selectivity with m-chloroperoxybenzoic acid. The basis for these selectivities is hydrogen bonding between the 3-substituent and the peracid.

Original languageEnglish (US)
Pages (from-to)5809-5812
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number32
DOIs
StatePublished - Aug 8 1994

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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