The bora-ene reaction of sulfur dioxide and prop-2-ene-1-boronic esters. New route to sulfoxides

  • Turks M
  • Lawrence A
  • Vogel P
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Abstract

A new one-pot synthesis of sulfoxides is presented. It involves the bora-ene reaction of sulfur dioxide and prop-2-ene-1-boronic esters, giving mixed anhydrides of sulfinic and boric acids. The latter react chemoselectively at the sulfur center with Grignard reagents in displacement reactions giving the corresponding prop-2-en-1-ylsulfoxides. Preliminary studies on the chirality transfer of enantiomerically enriched boronates to the sulfoxides are also presented. © 2006 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • Allylsulfoxide
  • Boronic ester
  • Chirality transfer
  • Ene-reaction
  • Grignard reagents

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