161. C−H Activation as a Strategic Reaction:  Enantioselective Synthesis of 4-Substituted Indoles

Authors: Huw M. L. Davies and James R. Manning

J. Am. Chem. Soc.,

2006, 128 (4), 1060–1061


A method is described for the asymmetric synthesis of 4-substituted indoles from the Rh2(S-DOSP)4-catalyzed decomposition of vinyldiazoacetates in the presence of N-Boc-4-acetoxy-6,7-dihydroindole. The reaction proceeds via a combined C−H activation/Cope rearrangement-elimination mechanism resulting in good yields and very high asymmetric induction.

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