Organocatalytic Asymmetric Reduction of δ‐Nitro Dienes: a Viable Entry to Functionalized Amines and Highly Substituted Enantioenriched Cyclopentanes

Abstract

Abstractδ‐nitro dienes were successfully synthesized and converted to δ‐nitro alkenes with complete chemo and regioselectivity. The enantioselective organocatalytic reduction was also accomplished and afforded the product in up to 97 % e.e. The chiral nitro alkene was further elaborated and employed as starting material in a stereoselective cyclization reaction that led to an almost enantiomerically pure highly functionalised cyclopentane featuring 5 contiguous stereocenters.