187091-55-0Relevant articles and documents
A versatile approach to cis-5-substituted 4-hydroxy-2-pyrrolidinones: asymmetric synthesis of angiogenesis inhibitor streptopyrrolidine
Xiang, Shao-Hua,Yuan, Hong-Qiu,Huang, Pei-Qiang
scheme or table, p. 2021 - 2026 (2010/02/28)
A concise, flexible, and highly diastereoselective approach to cis-5-alkyl-4-hydroxy-2-pyrrolidinones 1 is described. The key step is an ammonium acetate-assisted catalytic hydrogenation of the enamides 9, derived in two steps from malimides 6a,b as we ha
An easy access to protected (4S, 5R)-5-alkyl-4-hydroxy-2-pyrrolidinones and their use as versatile synthetic intermediates
Huang, Pei Qiang,Wang, Shi Li,Ye, Jian Liang,Ruan, Yuan Ping,Huang, You Qing,Zheng, Hong,Gao, Jing Xing
, p. 12547 - 12560 (2007/10/03)
A versatile approach to enantiopure (4S, 5R)-5-alkyl-4-hydroxy-2- pyrrolidinones is described. The key steps involve a regioselective Grignard reagent addition to (S)-malimides, and diastereoselective reductive dehydroxylation of the resulting hemi-azaketals. The flexibility of this methodology has been demonstrated by the synthesis of (2R, 3R)-3-amino-1- benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, emonapride, and the unnatural enantiomer of the β-hydroxy-γ-amino acid residue of hapalosin in lactam form.