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

J Am Chem Soc. 2011 Feb 16;133(6):1650-3. doi: 10.1021/ja1093309. Epub 2011 Jan 25.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Carbon / chemistry*
  • Catalysis
  • Hydrogen / chemistry*
  • Indoles / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Rhodium / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Indoles
  • Carbon
  • Hydrogen
  • Rhodium