Enantiopure 5-alkyl-4-methyl-2(5H)-furanones reacted by [2+2] photochemical cycloaddition with several trialkylsilylacetylenes to afford regioselectively 3-oxabicyclo[3.2.0]hept-6-en-2-ones silylated at the vinylic C-7 atom. The possible reasons for such regioselectivity are discussed. The anti/syn stereoselectivity of the photocycloaddition depends on the nature of the alkyl group on the silicon atom in the starting silylacetylenes. The photochemical cycloaddition of 2(5H)-furanones to trialkylsilylacetylenes regioselectively afforded cyclobutenes fused with furanone systems.
Regioselective formation of silylated cyclobutenes by the photochemical [2+2] cycloaddition of 2(5H)-furanones to trialkylsilylacetylenes
D'AURIA, Maurizio;RACIOPPI, Rocco
2012-01-01
Abstract
Enantiopure 5-alkyl-4-methyl-2(5H)-furanones reacted by [2+2] photochemical cycloaddition with several trialkylsilylacetylenes to afford regioselectively 3-oxabicyclo[3.2.0]hept-6-en-2-ones silylated at the vinylic C-7 atom. The possible reasons for such regioselectivity are discussed. The anti/syn stereoselectivity of the photocycloaddition depends on the nature of the alkyl group on the silicon atom in the starting silylacetylenes. The photochemical cycloaddition of 2(5H)-furanones to trialkylsilylacetylenes regioselectively afforded cyclobutenes fused with furanone systems.File in questo prodotto:
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