Synthesis of new aza-bicyclic 2-isoxazolines by 1, 3-dipolar cycloaddition of endocyclic enecarbamates and enamides with nitrile oxides

VM de Almeida, RJ dos Santos, AJ da Silva Góes…

Index: de Almeida, Valderes Moraes; dos Santos, Rosiel Jose; da Silva Goes, Alexandre Jose; de Lima, Jose Gildo; Duarte Correia, Carlos Roque; de Faria, Antonio Rodolfo Tetrahedron Letters, 2009 , vol. 50, # 6 p. 684 - 687

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Citation Number: 9

Abstract

Novel aza-bicyclic 2-isoxazolines, 4, 5-dihydroisoxazole [5, 4-b] pyrrolidines, and 4, 5- dihydroisoxazole [5, 4-b] piperidines were synthesized in a highly regioselective manner through a 1, 3-dipolar cycloaddition reaction of 5-and 6-membered endocyclic enecarbamates and enamides with several nitrile oxides in good to excellent yields. Hydrogenolysis of 5-and 6-membered Cbz-cycloadducts led to secondary amines, which ...

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