Catalytic enantioselective reissert-type reaction: Development and application to the synthesis of a potent NMDA receptor antagonist (-)-L-689,560 using a solid- …

M Takamura, K Funabashi, M Kanai…

Index: Takamura, Masahiro; Funabashi, Ken; Kanai, Motomu; Shibasaki, Masakatsu Journal of the American Chemical Society, 2000 , vol. 122, # 26 p. 6327 - 6328

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Citation Number: 156

Abstract

Full details of the first catalytic enantioselective Reissert-type reaction are described. Utilizing the Lewis acid-Lewis base bifunctional catalyst 5 or 6 (9 mol%), the Reissert products were obtained in 57 to 99% yield with 54 to 96% ee. Electron-rich quinolines produced better yields and enantioselectivities than electron-deficient substrates. Kinetic studies indicated that the reaction should proceed via the rate-determining acyl ...

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