Stereoselective synthesis of 3-substituted phtalides via asymmetric transfer hydrogenation using well-defined ruthenium catalysts under neutral conditions

K Everaere, JL Scheffler, A Mortreux, JF Carpentier

Index: Everaere, Kathelyne; Scheffler, Jean-Luc; Mortreux, Andre; Carpentier, Jean-Francois Tetrahedron Letters, 2001 , vol. 42, # 10 p. 1899 - 1901

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Citation Number: 39

Abstract

The asymmetric transfer hydrogenation of methyl 2-acylbenzoates and 2-propyl 3- acetylpyridine-2-carboxylate in 2-propanol, in the absence of base, with presynthesized Ru- {β-amino alcohol) or Ru-{TsDPEN} true catalysts provides 3-alkylphtalides in high yields and 92–97% ee. The procedure is, however, not as efficient for the preparation of optically active 3-phenylphtalide.