Ruthenium-catalyzed [2+ 2] cycloaddition reactions of a 2-oxa-3-azabicyclo [2.2. 1] hept-5-ene with unsymmetrical alkynes

R Durham, J Mandel, N Blanchard…

Index: Durham, Robin; Mandel, Jeremie; Blanchard, Nicolas; Tam, William Canadian Journal of Chemistry, 2011 , vol. 89, # 12 p. 1494 - 1505

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Citation Number: 5

Abstract

Ruthenium-catalyzed [2+ 2] cycloaddition reactions of a 2-oxa-3-azabicyclo [2.2. 1] hept-5- ene with unsymmetrical alkynes were investigated. Yields of up to 90% were obtained though regioselectivity was modest. Select cycloadducts could be separated and used to access a highly functionalized [3.2. 0] bicyclic structure through reductive cleavage of the N– O bond. These ring-opened products displayed a chemical exchange phenomenon in 1D ...