Highly Diastereoselective and Enantioselective C−H Functionalization of 1,2-Dihydronaphthalenes: A Combined C−H Activation/Cope Rearrangement Followed by a Retro-Cope Rearrangement

Abstract

The Rh2(S-DOSP)4-catalyzed reaction of vinyldiazoacetates with dihydronaphthalenes results in a highly enantioselective (91-99.6% ee) and diastereoselective (>98% de) C-H functionalization. The apparent intermolecular C-H insertion was demonstrated to be a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement.