N-Acyl 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) tetraphenylborate salts as O-acylating agents

被引：15
|
作者：
Taylor, James E. [1 ]
Williams, Jonathan M. J. [1 ]
Bull, Steven D. [1 ]
机构：
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 32期
关键词：
Acylation; Alcohol; Ester; DBN; Tetraphenylborate; TRIFLUOROACETYLATING REAGENT; KINETIC RESOLUTION; ACETYLATING AGENT; CARBOXYLIC-ACIDS; BENZOYL CYANIDE; PRIMARY AMINES; EFFICIENT; SECONDARY; MILD; ACYLBENZOTRIAZOLES;
D O I：
10.1016/j.tetlet.2012.05.108
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Air-stable and crystalline N-acyl DBN tetraphenylborate salts have been shown to be effective O-acylating agents, reacting with both primary and secondary alcohols to give the corresponding esters in good yields. In the case of diols, the N-acyl DBN-BPh4 salts have been shown to acylate regioselectively the primary alcohol functionality in the presence of a secondary alcohol. The DBN hydrotetraphenylborate side product can be readily removed by filtration, providing the ester products without the need for further purification. (C) 2012 Elsevier Ltd. All rights reserved.
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收藏
页码：4074 / 4076
页数：3
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