Synthesis of 1,3-dioxin-4-ones and their use in synthesis. 21. Intramolecular photocycloaddition reactions of chiral spirocyclic dioxinones having ω-alkenyl groups at 3-position

Article abstract of DOI:10.3987/COM-89-S6

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>cycloaddition reactions.