Stereoselective Diels−Alder Reactions of Hexachlorocyclopentadiene with Chiral Alkenes: New Insights Into the “Inside-Alkoxy” Model of Stereoselectivity

Abstract

Hexachlorocyclopentadiene undergoes Diels−Alder reactions with dienophiles possessing allylic chiral centers with moderate to excellent anti selectivity. Ab initio calculations on model systems elucidate the origin of this stereoselectivity which follow the “inside-alkoxy” model.