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Communication | Special issue | Vol 30, No. 1, 1990, pp.217-221
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S6
Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. 21. Intramolecular Photo[2+2]cycloaddition Reactions of Chiral Spirocyclic Dioxinones Having ω-Alkenyl Groups at 3-Position

Masayuki Sato,* Yoshito Abe, Chikara Kaneko,* Toshio Furuya, and Noriyoshi Inukai

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

Abstract

Chiral spirocyclic dioxinones having an ω-alkenyl group at 3-position were synthesized and their intramolecular photo[2+2]cycloaddition reactions were examined. The results not only provide enantioselective synthetic route to 2S-acetonylcyclohexanecarboxylic acids but also clarify the reason why these dioxinones exhibit remarkable diastereofacial selectivities in both intra- and intermolecular photo[2+2]cycloaddtion reactions.