Intramolecular Diels–Alder reaction of cyclopenta-1, 3-diene derivatives generated in situ from 4-(pent-4-enyl) cyclopent-2-enone ethylene ketals

M Ohkita, H Kawai, T Tsuji

Index: Ohkita, Masakazu; Kawai, Hidetoshi; Tsuji, Takashi Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 3 p. 366 - 370

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Abstract

Intramolecular Diels–Alder reaction of cyclopenta-1, 3-diene derivatives 16 generated in situ from the corresponding 4-(pent-4-enyl) cyclopent-2-enone ethylene ketals 15 is investigated. 4-[(E)-5-(Ethoxycarbonyl) pent-4-enyl] cyclopent-2-enone ethylene ketal 15a and 4-(5, 5-dicyanopent-4-enyl) cyclopent-2-enone ethylene ketal 15b were prepared in 5 steps from cyclopent-2-enone ethylene ketal 5. Upon heating at 120 C, compound 15a ...