Rhodium carbenoid approach for introduction of 4-substituted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles

Org Lett. 2010 Mar 5;12(5):924-7. doi: 10.1021/ol9028385.

Abstract

An unusual rhodium carbenoid approach for introduction of 4-substituted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles is described. These studies show that (Z)-vinylcarbenoids have a greater tendency than (E)-vinylcarbenoids to react at the vinylogous position of the carbenoid rather than at the carbenoid center.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Butyrates / chemistry*
  • Indoles / chemistry*
  • Nitro Compounds / chemistry*
  • Organometallic Compounds / chemistry*
  • Pyrroles / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • 6-(nitrooxy)hexyl-(2z)-4-(acetyloxy)-3-(4-(methylsulfonyl)phenyl)-2-phenylbut-2-enoate
  • Butyrates
  • Indoles
  • Nitro Compounds
  • Organometallic Compounds
  • Pyrroles
  • Rhodium