Stereoselective methoxyselenenylation of acyclic allylic alcohol derivatives: A method for the synthesis of 1,3-anti-diols

Article abstract of DOI:10.1016/0040-4039(95)02408-5

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.