HIGHLY ENANTIOSELECTIVE REDUCTION OF MESO-CYCLIC-1,2-DICARBOXIMIDES. ASYMMETRIC SYNTHESIS OF BICYCLIC 2-PYRROLIDINONE AND ITS 5-HYDROXY CONGENER

DOI: 10.3987/COM-92-6307

Source and publish data:

Heterocycles p. 937 - 940 (1993)

Update date:2022-07-29

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Authors:

Matsuki, Kenji

Inoue, Hirozumi

Ishida, Akihiko

Takeda, Mikio

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Article abstract of DOI:10.3987/COM-92-6307

Bicyclic-5-hydroxy-2-pyrrolidinones (2a-f) were synthesized with high enantioselectivity by the reduction of meso-cyclic-1,2-dicarboximides (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).

Full text of DOI:10.3987/COM-92-6307

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