1996 Volume 54 Issue 3 Pages 166-175
The use of organoselenium reagents in organic synthesis is now commonly accepted as introducing new functional groups into organic substrates under extremely mild reaction conditions. One of the useful reaction involving organoselenium reagents is the trans-addition reaction across carbon-carbon double bonds. They are highly stereospecific, and subsequent oxidation normally leads to regioselective and stereospecific elimination of the selenoxide to yield olefins. Recent advances in this field were reviewed in the following three topics; (1) preparation of reactive electrophilic selenium reagent in situ from diphenyl diselenide using easily available oxidants and their applications to the addition reactions across carbon-carbon multiple bond. (2) the design of chiral selenium reagents and their application to the asymmetric methoxyselenenylation and intramolecular oxyselenenylation. (3), catalytic oxyselenenylation- deselenenylation reaction and the other several catalytic approach.
