Disparity in the tandem epoxide-allylic alcohol-[1,2]/[2,3]-Wittig rearrangement of cis- and trans-1-benzyloxy-3,4-epoxycyclopentane
Abstract
The influence of the relative stereochemistry of the epoxide and benzyloxy functionalities present in cis- 1 and trans-1-benzyloxy-3,4-epoxycyclopentane 3 on the tandem epoxide–allylic alcohol–[1,2]/[2,3]-Wittig rearrangement has been studied, together with the Wittig rearrangement of the intermediate alcohols 2 and 4.