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

Article abstract of DOI:10.1016/S0040-4039(00)97907-3

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.