The regio- and stereo-selective formation of allylic chlorides during the Overman rearrangement of trichloroacetimidates derived from certain brominated conduritols

Abstract

Microwave irradiation of imidate 2 at 165C affords a ∼3:1 mixture of the Overman rearrangement product 3 and the allylic chloride 4 (83% combined yield). Under the same conditions the deoxy-conduritol 6 gives a comparable mixture of compounds 7 and 8. T Show more