STEREOSELECTIVE METHOXYSELENENYLATION OF ACYCLIC ALLYLIC ALCOHOL DERIVATIVES - A METHOD FOR THE SYNTHESIS OF 1,3-ANTI-DIOLS

摘要

Reaction of secondary acyclic trans-allylic alcohol derivatives with PhSeBr in the presence of 2,6-di-t-butylpyridine in MeOH proceeded in a highly regio- and stereoselective manner and the subsequent reduction and deprotection of the resultant methoxyselenides afforded mostly 1,3-anti-diols. The methoxyselenenylation of the acetate derivative of the same allylic alcohol, on the other hand, gave several other isomers along with the 1,3-anti-diol derivative. [References: 10]