Diastereoselectivity studies on the photo-activated cycloaddition of 5-(1,2-dioxyethyl)-2(5H)-furanones to alkenes

©ARKAT-USA, Inc. A series of 2(5H)-furanones, bearing a 1,2-dioxyethyl substituent at the γ-carbonyl position, have been prepared and explored as substrates in photochemical reactions with alkenes. Compared to the simpler oxymethyl analogues, the homologation of the side chain is highly beneficial to the antifacial selectivity of the [2+2] cycloadditions. Most reactions occur in synthetically useful yields, giving access to new polyfunctionalized cyclobutane-fused furanones.