Zinc(II)-promoted reduction of ketones by 1-methyl-1,4-dihydropyridines

✍ Scribed by A. J. de Koning; H. J. Alberts-Jansen; J. Boersma; G. J. M. van der Kerk

• Book ID: 104588262
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 616 KB
• Volume: 99
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19800991006

✦ Synopsis

Abstract

Zinc(II) promotes the reduction of unactivated ketones and aldehydes by (methyl‐substituted) 1‐methyl‐1,4‐dihydropyridines. Coordination of the dihydropyridines to the metal, which occurs via their annular nitrogen atoms, is essential for hydrogen‐transfer. The reductions proceed best in apolar non‐aromatic solvents, which are unable to compete with the carbonyl group of the substrate for a coordination site at the metal. Virtually no hydrogen‐transfer takes place in the absence of Zn(II) salts or when zinc coordination complexes are used in which the metal is coordinatively saturated.

The results of this study are discussed in terms of a possible relationship with the role of zinc in alcohol dehydrogenases and metal‐catalyzed reductions in biomimetic systems.