Construction of the N1-C3 linkage stereogenic centers by catalytic asymmetric amination reaction of 3-bromooxindoles with indolines

Org Lett. 2014 May 2;16(9):2394-7. doi: 10.1021/ol5007423. Epub 2014 Apr 11.

Abstract

The catalytic asymmetric amination reaction of 3-bromooxindoles with indolines for the construction of the N1-C3 linkage stereogenic centers has been realized for the first time. Moreover, the racemic substrates (3-substituted indolines) were also applicable under the same chiral conditions. The newly developed method conveniently led to a formal synthesis of (+)-psychotrimine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Catalysis
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Indoles / chemistry*
  • Molecular Structure
  • Oxindoles
  • Stereoisomerism

Substances

  • Indole Alkaloids
  • Indoles
  • Oxindoles
  • psychotrimine
  • 2-oxindole
  • indoline