Telescoped synthesis of stereodefined pyrrolidines

Org Lett. 2013 Jul 5;15(13):3472-5. doi: 10.1021/ol401554y. Epub 2013 Jun 25.

Abstract

Telescoped and one-pot olefination/asymmetric functionalization approaches to disubstituted pyrrolidines (dr up to 99:1, up to 99% ee) have been developed using commercially available tetramisole (0.1 to 5 mol %). Using OTMS-quinidine as the Lewis base gives preferential access to an anti-configured pyrrolidine in high enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Alkylation
  • Lewis Bases / chemistry*
  • Molecular Structure
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Stereoisomerism
  • Tetramisole / chemistry*

Substances

  • Alkenes
  • Lewis Bases
  • Pyrrolidines
  • Tetramisole