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

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.


Published in:
Tetrahedron Letters, 47, 16, 2783-2786
Year:
2006
Other identifiers:
Laboratories:




 Record created 2007-08-02, last modified 2018-03-17


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