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.
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页码：1071 / 1075
页数：5
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