Synthesis of substituted pyrrolin-4-ones from amino acids in mild conditions via a gold-catalyzed approach

J Org Chem. 2009 Aug 7;74(15):5614-7. doi: 10.1021/jo900693a.

Abstract

The gold-catalyzed cyclization of various alpha-amino-ynone derivatives gave the corresponding pyrrolin-4-ones in high yields. Moreover, the use of gold(III) oxide as catalyst allows a moderate to total stereocontrol during the cyclization. These pyrrolin-4-ones are highly useful intermediates for the synthesis of functionalized pyrrolidines and other natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Catalysis
  • Gold / chemistry*
  • Molecular Conformation
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Stereoisomerism

Substances

  • Amino Acids
  • Pyrroles
  • pyrroline
  • Gold