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Communication | Regular issue | Vol 36, No. 5, 1993, pp.937-940
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6307
Highly Enantioselective Reduction of meso-Cyclic-1,2-dicarboximides. Asymmetric Synthesis of Bicyclic 2-Pyrrolidinone and Its 5-Hydroxy Congener

Kenji Matsuki,* Hirozumi Inoue, Akihiko Ishida, Mikio Takeda, Masako Nakagawa, and Tohru Hino

*Organic Chemistry Research Laboratory, Tanabe Seiyaku Co.Ltd., 2-2-50, Kawagishi, Toddda, Saitama 335-8505, Japan

Abstract

Bicyclic 5-hydroxy-2-pyrrolidinones (2a-f) were synthesized with high enantioselectivity by the reduction of meso-cyclic-1,2-dicarboxiamides (1a-f) with lithium aluminum hydride (LiAlH4)-methanol (MeOH)-1,1’-bi-2-naphthol complex (BINAL-H). Treatment of 2a-f with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave optically active 2-pyrrolidinones (3a-f) in quantitative yields. For the absolute configuration correlation, 2a-d were converted into known lactones (4a-d).