Chemistry of sulfines, part V: Chemo- and stereoselective synthesis and hetero-diels-alder reactions of stable sulfines

Ahmed A. El Gokha, Omar M. Ali, Ibrahim F. Zeid, Takayuki Kudoh, Ibrahim El-Sayed

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The stereoselective synthesis of a variety of Z-sulfines by the oxidation of organic trithiocarbonates with m-chloroperbenzoic acid (m-CPBA) is described. Transient E-sulfines that are formed upon heating of Z-sulfines during cycloaddition reactions were trapped with 2,3-dimethyl-1,3-butadiene to yield only one of the possible diastereomers of the functionalized cyclic allylic sulfoxides. An X-ray analysis and ab initio calculations were performed to provide insight into the steric course of the oxidation and cycloaddition reactions. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional tables and figures.]

Original languageEnglish
Pages (from-to)185-197
Number of pages13
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume189
Issue number2
DOIs
Publication statusPublished - Jan 1 2014

Keywords

  • 1,3-dienes
  • Ab initio calculations
  • Chlorodithioformates
  • Diels-Alder
  • X-ray
  • oxidation
  • sulfines
  • thiopyran S-oxides
  • trithiocarbonates

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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