Boronic acid catalysis for mild and selective [3+ 2] dipolar cycloadditions to unsaturated carboxylic acids

H Zheng, R McDonald, DG Hall

Index: Zheng, Hongchao; McDonald, Robert; Hall, Dennis G. Chemistry - A European Journal, 2010 , vol. 16, # 18 p. 5454 - 5460

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Citation Number: 53

Abstract

Abstract Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3+ 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid ...