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

Authors: Huw M. L. Davies and Qihui Jin

J. Am. Chem. Soc.,

2004, 126 (35), 10862–10863


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.

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