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.
Regioselective Formation of Silylated Cyclobutenes by the Photochemical [2+2] Cycloaddition of 2(5H)-Furanones to Trialkylsislylacetylenes / D'Annibale, Andrea; Maurizio, D'Auria; Giovanna, Mancini; Alessio Daniel, Pace; Rocco, Racioppi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - (2012), pp. 785-791. [10.1002/ejoc.201101332]
Regioselective Formation of Silylated Cyclobutenes by the Photochemical [2+2] Cycloaddition of 2(5H)-Furanones to Trialkylsislylacetylenes
D'ANNIBALE, Andrea;
2012
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
