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Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles.

ABSTRACT: A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh(2)(S-NTTL)(4), the putative Rh-carbene intermediates from ?-alkyl-?-diazoesters react with indoles at C(3) to provide ?-alkyl-?-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh-ylide intermediate with oxocarbenium character.

SUBMITTER: DeAngelis A

PROVIDER: S-EPMC3144986 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles.

DeAngelis Andrew A Shurtleff Valerie W VW Dmitrenko Olga O Fox Joseph M JM

Journal of the American Chemical Society 20110125 6

A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh(2)(S-NTTL)(4), the putative Rh-carbene intermediates from α-alkyl-α-diazoesters react with indoles at C(3) to provide α-alkyl-α-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh-ylide intermediate with oxocarbenium character. ...[more]

PMID: 21265565

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