Solvent effects on the diastereoselection in LiAlH4 reduction of α-substituted ketones

被引：12

作者：

Suzuki, Yasumitsu ^{[1
]}

Kaneno, Daisuke ^{[1
]}

Miura, Masaya ^{[1
]}

Tomoda, Shuji ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Arts & Sci, Dept Life Sci, Meguro Ku, Tokyo 1538902, Japan

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 27期

基金：

日本学术振兴会;

关键词：

LiAlH4; reduction; diastereoselection; chelation model; solvent effect;

D O I：

10.1016/j.tetlet.2008.05.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Based on high-level DFT calculations including solvent molecules, it was found that steric effects of solvent may be responsible for the diastereoselection in LiAlH4 reduction of acyclic ketones substituted by an oxygen-containing functional group at the alpha-position to the carbonyl. It was concluded that the conventional chelated transition state models lead to the predominance of the R*,S*-diastereoisomers against experimental observation. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：4223 / 4226

页数：4

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