Multiple component reactions: an efficient nickel-catalyzed Reformatsky-type reaction and its application in the parallel synthesis of beta-amino carbonyl libraries

J Org Chem. 2003 Mar 21;68(6):2143-50. doi: 10.1021/jo026847q.

Abstract

Multiple-component condensations (MCC) where three or more reactants combine to afford a new core structure possessing the molecular features of its composite building blocks is a powerful method for the preparation of molecular diversity. We have developed an efficient, nickel-catalyzed, Reformatsky-type three-component condensation (3CC) reaction that affords beta-amino carbonyl compounds. The scope of the reaction is demonstrated both in the gram and microscale settings; 15 beta-amino esters, amides, and a ketone were prepared efficiently at the mmol scale, and a library of 64 beta-amino carbonyl compounds was generated at the micromol scale.

Publication types

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

MeSH terms

  • Amines / chemistry*
  • Carbonic Acid / chemistry*
  • Catalysis
  • Chromatography, Thin Layer
  • Combinatorial Chemistry Techniques*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nickel / chemistry*
  • Stereoisomerism

Substances

  • Amines
  • Carbonic Acid
  • Nickel