Retentive Stereospecificity in Deoxygenation of Epoxides with Sn-Al Reagents

Article abstract of DOI:10.1246/bcsj.58.1480

Reaction of epoxides with 3SnAlMe₃>(1-)*Li(1+) affords β-oxido stannanes which collapse to alkene with overall retention of stereochemistry.The S_N2 type ring opening of epoxides by tributylstannyl anion followed by anti elimination of Bu₃Sn and OAl^-Me₃ groups explains the stereochemical results.The method can be succesfully applied to hydroxy epoxides derived from (E)-2-nonen-1-ol.The deoxygenation of epoxides with PhMe₂SiAlEt₂ also provides olefins of the same geometry as epoxides.