C-H activation as a strategic reaction: enantioselective synthesis of 4-substituted indoles

Huw M L Davies; James R Manning

doi:10.1021/ja057768+

C-H activation as a strategic reaction: enantioselective synthesis of 4-substituted indoles

J Am Chem Soc. 2006 Feb 1;128(4):1060-1. doi: 10.1021/ja057768+.

Authors

Huw M L Davies¹, James R Manning

Affiliation

¹ Department of Chemistry, University at Buffalo, The State University of New York, 14260-3000, USA. [email protected]

PMID: 16433506
DOI: 10.1021/ja057768+

Abstract

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Catalysis
Indoles / chemical synthesis*
Indoles / chemistry
Organometallic Compounds / chemistry
Proline / analogs & derivatives
Proline / chemistry
Stereoisomerism

Substances

Indoles
Organometallic Compounds
dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate)
Proline