Highly enantioselective catalytic acyl-pictet-spengler reactions

J Am Chem Soc. 2004 Sep 1;126(34):10558-9. doi: 10.1021/ja046259p.

Abstract

The enantioselective cyclization of N-acyliminium ions generated in situ from tryptamine is promoted with high enantioselectivity by a new chiral thiourea catalyst. This represents the first successful system for asymmetric catalysis of the Pictet-Spengler reaction.

Publication types

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

MeSH terms

  • Carbolines / chemical synthesis*
  • Catalysis
  • Cyclization
  • Hydrogen Bonding
  • Imines / chemistry
  • Indole Alkaloids / chemical synthesis
  • Stereoisomerism
  • Thiourea / analogs & derivatives*
  • Thiourea / chemistry

Substances

  • Carbolines
  • Imines
  • Indole Alkaloids
  • Thiourea