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Communication | Regular issue | Vol 31, No. 12, 1990, pp.2115-2119
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5605
Regio- and Stereocontrols in the Photo[2+2]cycloaddition of 1,3-Dioxin-4-ones to Alkenes. Use of an Ester Group as the Connecting Unit in the Intramolecular Variant

Masayuki Sato,* Yoshito Abe, Hirohide Ohuchi, and Chikara Kaneko*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Intramolecular photo[2+2]cycloaddition of dioxinones to alkene to give eight membered lactones proceeds with complete stereo- and high regioslelctivities when an ester group presents as a linking unit between the acetal carbon and double bond of the side chain. The successful separation of some dioxinones into the enantiomers indicates the method is useful for synthesis of enantiomerically pure compounds.