Regiocontrol in the 1, 3-dipolar cycloaddition reactions of mesoionic compounds with acetylenic dipolarophiles

BP Coppola, MC Noe, SSK Hong

Index: Coppola, Brian P.; Noe, Mark C.; Hong, Sam Shih-Kuang Tetrahedron Letters, 1997 , vol. 38, # 41 p. 7159 - 7162

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Citation Number: 17

Abstract

The regioselectivity of 1, 3-dipolar cycloaddition reactions between mesoionic compounds with singly-tethered substituents is examined. The results with propiolate dipolarophiles are compared with other singly and doubly-tethered examples according to a model using an asynchronous, concerted transition state. The isolation and reaction of a novel, nonaryl substituted mesoionic compound 7 is reported. A regiodirected synthesis starting with N-(2 ...