151710-41-7Relevant academic research and scientific papers
HIGHLY ENANTIOSELECTIVE REDUCTION OF MESO-CYCLIC-1,2-DICARBOXIMIDES. ASYMMETRIC SYNTHESIS OF BICYCLIC 2-PYRROLIDINONE AND ITS 5-HYDROXY CONGENER
Matsuki, Kenji,Inoue, Hirozumi,Ishida, Akihiko,Takeda, Mikio
, p. 937 - 940 (1993)
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).
Enantioselective reduction of meso-cyclic-1,2-dicarboxylic anhydrides and 1,2-dicarboximides: Asymmetric synthesis of bicyclic lactones and hydroxylactams
Matsuki,Inoue,Ishida,Takeda,Nakagawa,Hino
, p. 9 - 18 (2007/10/02)
Chiral bicyclic lactones (3,8,9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1,2- dicarboxylic anhydrides (1, 4) and meso-cyclic-1,2-dicarboximides (2) with lithium aluminum hydride (LiAlH4)-alcohol(ROH)-(R)- or (S)-1,1'-bi-2- naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.
