Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles |
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Authors: | DeAngelis Andrew Shurtleff Valerie W Dmitrenko Olga Fox Joseph M |
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Institution: | Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States. |
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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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