Mechanistic rationale for the NaBH4 reduction of α-keto esters

被引：27
作者：
Dalla, V
Catteau, JP
Pale, P
机构：
[1] Univ Sci & Technol, Associe CNRS, Lab Chim Organ & Macromol, F-59655 Villeneuve Dascq, France
[2] Univ Strasbourg, Inst Le Bel, Lab React & Synthese Organ, F-67000 Strasbourg, France
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 28期
关键词：
D O I：
10.1016/S0040-4039(99)01006-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An intramolecular hydride delivery process largely contributes during the double reduction of alpha-keto esters into diols by NaBH4. In the cast of enolic alpha-keto esters, me first step of the process, the reduction of the keto group, occurred exclusively through an 1,2-hydride addition despite the predominance of me tautomeric enolic form The clear-cut difference of reaction rate between coolie and non enolic substrate 4 for reaction carried out in methanol is interpreted in terms of competitive hydride consumption due to the extremely favorable reaction between this solvent and NaBH4. (C) 1999 Elsevier Science Ltd. All rights reserved.
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收藏
页码：5193 / 5196
页数：4
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