A Catalytic, Me2Zn-Mediated, Enantioselective Reformatsky Reaction With Ketones

✍ Scribed by Pier Giorgio Cozzi

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 102 KB
• Volume: 118
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/ange.200504239

✦ Synopsis

on the occasion of his 70th birthday

The Reformatsky reaction, [1] one of the classic "named" reactions, was discovered almost 120 years ago and is still widely used in synthesis. [2] It consists of the zinc-induced formation of b-hydroxyalkanoates from a-halocarbonyl compounds and aldehydes or ketones. Its excellent functional group tolerance and the possibility of preparing the reagent in situ, by activation of zinc metal following a variety of different methods, [3] have contributed to its success. In the last six years, homogeneous Reformatsky-type reactions based on the use of Me 2 Zn or Et 2 Zn in the presence of nickel [4] or rhodium [5] have been described.

Although progress has been made on an asymmetric version of the Reformatsky reaction with the introduction of chiral auxiliaries [6] or ligands, [7] a truly catalytic version has still not been achieved. Very few methods have been reported