Multiple component reactions: an efficient nickel-catalyzed Reformatsky-type reaction and its application in the parallel synthesis of beta-amino carbonyl libraries.
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.
Adrian
James C
JC
Chemistry Department, Union College, Schenectady, New York 12308, USA. adrianj@union.edu
Snapper
Marc L
ML
D000588:Amines / Q000737:chemistry*; D002255:Carbonic Acid / Q000737:chemistry*; D002384:Catalysis; D002855:Chromatography, Thin Layer; D020650:Combinatorial Chemistry Techniques; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D002255:Carbonic Acid; D009532:Nickel