ChemInform Abstract: An Easy Access to Protected (4S,5R)-5-Alkyl-4-hydroxy-2-pyrrolidinones and Their Use as Versatile Synthetic Intermediates

Autor:	Hong Zheng, Pei-Qiang Huang, Yishun Huang, Jing Xing Gao, Yuan-Ping Ruan, Shao-pei Wang, Jian Liang Ye
Rok vydání:	2010
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Residue (chemistry) Enantiopure drug Chemistry Diamine Lactam Regioselectivity General Medicine Pyrrolidinones Enantiomer Combinatorial chemistry Alkyl
Zdroj:	ChemInform. 30
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.199904114
Popis:	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.
Databáze:	OpenAIRE
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