Asymmetric Diels–Alder reactions of a chiral sugar nitroalkene: diastereofacial selectivity and regioselectivity
Abstract
The uncatalysed Diels–Alder addition of 1 -(trimethylsilyloxy)- and 1 -acetoxybuta-1,3-diene to a sugar-derived nitroalkene proceeds with complete regioselectivity and diastereofacial selectivity to yield crystalline, optically pure, cyclohexene derivatives.