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 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.

SUBMITTER: DeAngelis A 

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

REPOSITORIES: biostudies-literature