Weissenberg, M., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel Krinsky, P., Faculty of Agriculture, Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76-100, Israel Glotter, E., Faculty of Agriculture, Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76-100, Israel
The epoxide ring in steroidal trans-αβ and βy-epoxy-alcohols is cleaved by sodium borohydride in refluxing methanol to give the corresponding methoxyhydrins, in contrast to the cis-epoxy-alcohols which remain unchanged. The steric requirements of the reaction and a mechanism involving the intermediate formation of a boron complex with the substrate are discussed.
Cleavage of the epoxide ring in trans-epoxy-alcohols by sodium borohydride in methanol
Weissenberg, M., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel Krinsky, P., Faculty of Agriculture, Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76-100, Israel Glotter, E., Faculty of Agriculture, Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76-100, Israel
Cleavage of the epoxide ring in trans-epoxy-alcohols by sodium borohydride in methanol
The epoxide ring in steroidal trans-αβ and βy-epoxy-alcohols is cleaved by sodium borohydride in refluxing methanol to give the corresponding methoxyhydrins, in contrast to the cis-epoxy-alcohols which remain unchanged. The steric requirements of the reaction and a mechanism involving the intermediate formation of a boron complex with the substrate are discussed.