Masked amino acid: a new C-nucleophile for I2-catalyzed stereoselective ring opening of epoxides in ionic liquid

被引：15

作者：

Rai, Vijai K. ^{[1
,2
]}

Sharma, Roopali ^{[2
]}

Kumar, Anil ^{[2
]}

机构：

[1] Inst Technol, Dept Appl Chem, Bilaspur 495009, Chattisgarh, India

[2] Shri Mata Vaishno Devi Univ, Sch Biol & Chem, Katra 182332, JK, India

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 09期

关键词：

Epoxide; Ionic liquid; Nucleophile; Stereoselectivity; Iodine; HIGHLY EFFICIENT SYNTHESIS; FRIEDEL-CRAFTS ALKYLATION; BASE-CATALYZED ADDITION; ACETONE CYANOHYDRIN; HIGHER-ORDER; ENANTIOSELECTIVE ADDITION; KNOEVENAGEL CONDENSATION; AROMATIC EPOXIDES; GAMMA-LACTONES; MESO EPOXIDES;

D O I：

10.1016/j.tetlet.2012.12.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first one-pot molecular iodine catalyzed direct aminoacetylation of terminal epoxides in ionic liquid [bmim]OH is reported. Herein, 2-phenyl-1,3-oxazolon-5-one and a variety of terminal epoxides afford 3(N-substituted)aminofuran-2-ones in high yield (84-95%) and excellent cis diastereoselectivity (>94%) via ring-opening of terminal epoxides and aminoacetylative cyclization cascade. Operation simplicity, absence of by-product formation, and ambient temperature are the salient features of the present synthetic protocol. After isolation of the product, the ionic liquid [bmim]OH could be easily recycled for further use without any loss of efficiency. (C) 2012 Elsevier Ltd. All rights reserved.

引用

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页码：1071 / 1075

页数：5

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