Rhodium-catalyzed [3 + 2] annulation of indoles

J Am Chem Soc. 2010 Jan 20;132(2):440-1. doi: 10.1021/ja9078094.

Abstract

An effective Rh(2)(S-DOSP)(4)-catalyzed asymmetric cyclopentannulation of indolyl rings has been developed. Depending on the substitution pattern of the indole, two distinct regioisomeric products can be generated. These studies demonstrate that rhodium-catalyzed reactions of donor/acceptor carbenoids proceeding by means of zwitterionic intermediates can be carried out with very high asymmetric induction.

Publication types

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

MeSH terms

  • Catalysis
  • Cyclization
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Indoles
  • Organometallic Compounds
  • indoline
  • Rhodium