A catalytic, Me2Zn-mediated, enantioselective reformatsky reaction with ketones
A catalytic, Me2Zn-mediated, enantioselective reformatsky reaction with ketones
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DOI：
10.1002/anie.200504239
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发表时间：
2006-01-01
影响因子：
16.6
通讯作者：
Cozzi, Pier Giorgio
中科院分区：
文献类型：
--
作者：
Cozzi, Pier Giorgio
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 β-hydroxyalkanoates from α-halocarbonyl compounds and aldehydes or ketones. Its excellent functional group tolerance and the possibility of preparing the reagent insitu, 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 Me2Zn or Et2Zn 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 [*] Prof. Dr. PG Cozzi Dipartimento di Chimica “G. Ciamician” Università di Bologna Via Selmi, 2, 40126 Bologna (Italy) Fax:(+ 39) 051-209-9456 E-mail: piergiorgio. cozzi@ unibo. it [**] Dr. Eleonora Rivalta is acknowledged for her experimental help. Professor Giuseppe Bartoli and Dr. Paolo Melchiorre are acknowledged for allowing use of their chiral GC instruments. The European Commission (project FP6-505267-1 (LIGBANK)), MIUR (Progetto Nazionale Stereoselezioni in Chimica Organica: Metodologie ed Applicazioni), and FIRB (Progettazione, preparazione e valutazione biologica e farmacologica di nuove molecole organiche quali potenziali farmaci innovativi) are acknowledged for their financial support of this research.
