Anion-induced enantioselective cyclization catalyzed by cationic gold catalysts

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In this thesis the first highly enantioselective functionalization of terminal alkynes using gold(I) catalysts incorporating optically active counteranions is described. Cationic gold(I) catalysis was used in a novel asymmetric synthesis of substituted pyrrolidines, 2,3-dihydro-1H-pyrroles, and tetrahydrofurans from 1,4-diynamides, 1,6- diynamides, and 1,4-diynols, respectively. The role of counteranions in these transformations was studied and their employment found to be crucial for high selectivities. Utilizing the newly-developed catalytic system allows an access to the products in near quantitative yields and in good to excellent enantiomeric excesses.