A new approach to asymmetric synthesis of polycycles on the basis of o-quinodimethane generation

…, Y Amino, M Nakatsuka, T Saegusa

Index: Ito, Yoshihiko; Amino, Yusuke; Nakatsuka, Masashi; Saegusa, Takeo Journal of the American Chemical Society, 1983 , vol. 105, # 6 p. 1586 - 1590

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Citation Number: 52

Abstract

Abstract: The fluoride anion induced 1, 4 elimination of 2-[o-[l-(trimethylsilyl) alkyl] phenyl]-3, 3-dimethyloxazolidinium salts generates (E, E)-a-alkyl-a/-[2-(dimethylamino) alkyl]-0- quinodimethane intermediates, which are trapped stereoselectively with dienophiles to give polycycles. Intramolecular cyclization of 2-[o-[I-(trimethylsilyl) hept-6-enyl] phenyl]-3, 3- dimethyl-4-