Thiourea catalyzed aminolysis of epoxides under solvent free conditions. Electronic control of regioselective ring opening

被引：29

作者：

Chimni, Swapandeep Singh ^{[1
]}

Bala, Neeraj ^{[1
]}

Dixit, Vaibhav A. ^{[2
]}

Bharatam, Prasad V. ^{[2
]}

机构：

[1] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India

[2] Natl Inst Pharmaceut Educ & Res, Dept Med Chem, Sector 67, Sas Nagar 160062, Punjab, India

来源：

TETRAHEDRON | 2010年 / 66卷 / 16期

关键词：

ASYMMETRIC AMINOHYDROXYLATION; EFFICIENT METHOD; ANALOGS; AMINES; ORGANOCATALYSIS; ALCOHOLS; TRIFLATE; DESIGN; PROTON;

D O I：

10.1016/j.tet.2010.02.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A reactant economizing process for the regioselective aminolysis of epoxides using equimolar quantities of reactants catalyzed by the double hydrogen bond donor N,N'-bis[3,5-bis(trifluoromethyl)phenyl]thiourea is reported. Regioselectivity of the reaction is controlled by the electronic nature of the substituent on the styrene oxide, which has been substantiated on the basis of C-13 NMR data and DFT calculations. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3042 / 3049

页数：8

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