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.
Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield S3 7HF, UK. simon.jones@sheffield.ac.uk
Simon
S
Jones
Damien
D
Valette