Lewis acid catalyzed acylation reactions: scope and limitations

被引：155

作者：

Chandra, KL ^{[1
]}

Saravanan, P ^{[1
]}

Singh, RK ^{[1
]}

Singh, VK ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON | 2002年 / 58卷 / 07期

关键词：

acylation reactions; alcohols; thiols; phenols and sugars; copper triflate; tin triflate; acetic anhydride;

D O I：

10.1016/S0040-4020(01)01229-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Acylation of alcohols, thiols, and sugars were studied with a variety of Lewis acids, and it was found that Cu- and Sn(OTf)(2) are very efficient in catalyzing the reaction under mild conditions. Among these two catalysts, Cu(OTf)(2) was preferred because of its lower cost and relatively higher yield of the acylated product. The reaction was studied in several solvents, but CH2Cl2 was preferred. It was also observed that the present method is suitable for acylation of tertiary alcohols. Sugars were also acylated without any epimerization at the anomeric center. It is further shown here that this method is also suitable for selective acylation of primary or secondary alcohols over tertiary ones. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1369 / 1374

页数：6

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