Asymmetric Tandem Reaction of Dicyanoalkenes with Conjugated Sulfinyl Imino Esters

Abstract

An asymmetric tandem reaction of α,α-dicyanoalkenes and enantiomerically pure α,β-unsaturated N-sulfinyl imino esters is reported herein. It involves a four step-protocol that ends up in the generation of a new family of tetracyclic products in a diastereoselective fashion. The overall process takes place in good yields and moderate to good enantioselectivities, and entails the formation of three bonds and four stereocenters. A plausible reaction mechanism has also been proposed.