Asymmetric ruthenium-catalyzed [2+2] cycloadditions between bicyclic alkenes and chiral alkynes

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Authors

Goodreid, Jordan

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University of Guelph

Abstract

Transition metal-catalyzed cycloaddition reactions are among some of the most powerful methods available for the construction of ring systems in organic synthesis. This thesis is an investigation of an asymmetric version of the ruthenium-catalyzed [2+2] cycloaddition between bicyclic alkenes and alkynes which bear the acetylenic acyl camphorsultam chiral auxiliary. Cycloaddition reactions between norbomene and a variety of aryl- and alkyl-substitued alkynes bearing the acetylenic acyl sultam were found to proceed in excellent yields (up to 99 %) and diastereoselectivities (up to d.r. = 131 : 1), depending on the choice of solvent, temperature, and the steric and electronic properties of the unsaturated reacting partners. The chiral auxiliary approach to the ruthenium-catalyzed [2+2] cycloaddition has been shown to be a mild and effective method for the asymmetric construction of substituted cyclobutene ring systems.

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Keywords

transition metal-catalyzed reactions, cycloaddition reactions, ring systems, organic synthesis, asymmetric, ruthenium-catalyzed [2+2] cycloaddition, bicyclic alkenes, alkynes, acetylenic acyl camphorsultam, chiral auxiliary

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