Enantioselective Synthesis of Allylic Alcohols via an Oxazaborolidinium Ion Catalyzed Diels—Alder/retro-Diels—Alder Sequence.

A triflimide-activated oxazaborolidine catalyst successfully promoted the asymmetric Diels-Alder reaction of 9-methylanthracene with methacrolein in high regio- and enantioselectivity. The cycloadduct obtained was subsequently used as a chiral template to access secondary and tertiary allylic alcohols in good to high enantiomeric excess via a cycloreversion by flash vacuum pyrolysis.