Recognition-mediated regiocontrol of a dipolar cycloaddition reaction

被引:60
作者
Howell, SJ
Spencer, N
Philp, D [1 ]
机构
[1] Univ St Andrews, Sch Chem, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland
[2] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
基金
英国工程与自然科学研究理事会;
关键词
azides; cycloaddition; kinetics; molecular recognition;
D O I
10.1016/S0040-4020(01)00402-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The rational design of a recognition-based system that is capable of accelerating and controlling the regiochemical outcome of a dipolar cycloaddition reaction between an azide and an alkyne is presented. The origins of the acceleration and control of the cycloaddition reactions are rationalized-using molecular mechanics calculations-in terms of the formation of a complex between the reagents which organizes and orients them prior to reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4945 / 4954
页数:10
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