Telluride-mediated stereospecific conversion of racemic E-allylic alcohols to homochiral Z-allylic alcohols; transposition of primary and secondary allylic alcohols via glycidol derivatives

Abstract Racemic trans -secondary allylic alcohols can be converted to homochiral cis -secondary allylic alcohols by means of a telluride-mediated transposition reaction applied to the homochiral glycidol obtained from a Sharpless kinetic resolution. (+)-Linalool is obtained in >95% enantiomeric excess from geraniol, an example of a transposition of a primary allylic alcohol to a homochiral tertiary alcohol.