Ethylene in organic synthesis: a new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation

Org Lett. 2011 Dec 16;13(24):6596-9. doi: 10.1021/ol203052y. Epub 2011 Nov 21.

Abstract

The asymmetric hydrovinylation (1 mol % Ni-cat., 1 atm, ethylene, >98% ee) products from 1-methylenetetralines are readily converted into 3,3-disubstituted oxindoles and subsequently to pyrrolidinoindolines. These hydrovinylation products are also useful for the syntheses of enantiopure benzomorphans.

Publication types

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

MeSH terms

  • Catalysis
  • Ethylenes / chemistry*
  • Indoles / chemistry*
  • Molecular Structure
  • Oxindoles
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Stereoisomerism

Substances

  • Ethylenes
  • Indoles
  • Oxindoles
  • Pyrrolidines
  • 2-oxindole
  • ethylene