Robert P. Discordia

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.

2-Substituted-4-hydroxymethyltellurophenes from acetylenic epichlorohydrins and sodium telluride

Abstract 2-Substituted-4-hydroxymethyltellurophenes and acetylenic allyl alcohols (enynols) are products from the action of sodium telluride on acetylenic epichlorohydrins. Variation in the degree of reduction of tellurium to telluride ion has a dramatic effect on the ratio of tellurophene to allyl alcohol, either of which may be obtained as the major product.