A chiral auxiliary derived from levoglucosenone in assymetric Diels-Alder transformations

Abstract

The Diels-Alder reaction of the acrylate derived from levoglucosenone with cyclopentadiene was studied under several conditions, in the presence and absence of a Lewis acid. The results showed satisfactory diastereomeric excess and the ratio of cycloadducts was found to depend on the reaction conditions. A reversal in stereoselectivity was observed when EtAlCl2 or Et 2AlCl were employed as Lewis acids.