Synthesis of β-hydroxy nitriles and 1,3-amino alcohols from epoxides using acetone cyanohydrin as a LiCN precursor

被引：26

作者：

Ciaccio, JA ^{[1
]}

Smrtka, M ^{[1
]}

Maio, WA ^{[1
]}

Rucando, D ^{[1
]}

机构：

[1] Fordham Univ, Dept Chem, Bronx, NY 10458 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 39期

基金：

美国国家科学基金会;

关键词：

epoxide; lithium cyanide; beta-hydroxy nitrile; amino alcohol; one-pot; anhydrous conditions;

D O I：

10.1016/j.tetlet.2004.08.039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of acetone cyanohydrin with MeLi affords a LiCN(.)acetone complex that can be made to react with epoxides in THF, either in one-pot or using isolated samples of the cyanide complex, to cleanly afford beta-hydroxy nitriles upon aqueous workup; in situ hydride reduction of nitriles affords 1,3-amino alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：7201 / 7204

页数：4

共 27 条

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CHEN RY, 1995, SCI CHINA SER B, V38, P152

[2] EASY DIRECT STEREOSELECTIVE AND REGIOSELECTIVE FORMATION OF BETA-HYDROXY NITRILES BY REACTION OF 1,2-EPOXIDES WITH POTASSIUM CYANIDE IN THE PRESENCE OF METAL-SALTS [J].