Enantioselective Double C-H Activation of Dihydronaphthalenes
H. M. L. Davies*, Q. Jin
University at Buffalo, The State University of New York, USA
21. September 2005 (online)
A formal C-H activation of 1,2-dihydronaphthalenes was observed using dirhodium tetrakis[(S)-N-dodecylbenzenesulfonyl]prolinate [Rh2(S-DOSP)4] and an excess of methyl vinyldiazoacetates. The postulated mechanism involves a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement. The generation of four new stereocenters occurred with excellent enantio- and diastereoselectivity.