Reduction of aromatic and aliphatic keto esters using sodium borohydride/MeOH at room temperature: a thorough investigation

被引：36
|
作者：
Kim, Juryoung [1 ]
De Castro, Kathlia A. [2 ]
Lim, Minkyung [1 ]
Rhee, Hakjune [1 ,2 ]
机构：
[1] Hanyang Univ, Dept Bionanotechnol, Ansan 426791, Kyunggi Do, South Korea
[2] Hanyang Univ, Dept Chem & Appl Chem, Ansan 426791, Kyunggi Do, South Korea
来源：
TETRAHEDRON | 2010年 / 66卷 / 23期
关键词：
Alcohols; Reduction; Esters; Keto esters; Sodium borohydride; ASYMMETRIC-SYNTHESIS; SELECTIVE REDUCTIONS; METAL-ION; CARBOXYLIC ESTERS; SEX-PHEROMONES; SLOW ADDITION; ALCOHOLS; METHANOL; ACETATE; SOLVENT;
D O I：
10.1016/j.tet.2010.04.062
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reduction of keto esters is a valuable alternative to produce diols. Sodium borohydride/MeOH system at room temperature and short reaction time efficiently reduced alpha, beta, gamma, and delta-keto esters having alpha-keto esters as the most reactive. The ester functionality was reduced effectively due to the presence of oxo group that somehow facilitates the formation of ring intermediate. As expected, the chemoselective experiments showed that ester functionality was not reduced using this system. This study presents a simple, easy, and benign reduction process of various keto esters to its corresponding diols. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3995 / 4001
页数：7
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