Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles
Journal of the American Chemical Society2011Vol. 133(6), pp. 1650–1653
Citations Over TimeTop 10% of 2011 papers
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.
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