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A series of 2(5 H)-furanones, bearing a 1,2-dioxyethyl substituent a t the γ-carbonyl position, have been prepared and explored as substrates in photoch emical 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 cyc lobutane-fused furanones.

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