Stereodivergent Synthesis of Enantioenriched 2-Pyrrolidones via Diastereoselective Hydrogenation of ?,?-Unsaturated ?-Lactams

被引：0
|
作者：
Guo, Siyuan [1 ,2 ]
Ma, Baode [1 ,2 ]
Chen, Gen-Qiang [3 ,4 ]
Zhang, Xumu [1 ,2 ]
机构：
[1] Southern Univ Sci & Technol, Med X Pingshan, Shenzhen 518000, Peoples R China
[2] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518000, Peoples R China
[3] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Peoples R China
[4] Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China
来源：
ORGANIC LETTERS | 2023年
基金：
国家重点研发计划; 中国国家自然科学基金;
关键词：
GAMMA-LACTAMS; PIRACETAM; DERIVATIVES;
D O I：
10.1021/acs.orglett.3c005322426Org
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthesis of optically enriched racetam analogues was achieved via highly remote diastereocontrolled and enantiocontrolled Pd/C-catalyzed hydrogenation of alpha,beta-unsaturated gamma-lactams. Various mono-and disubstituted 2-pyrrolidones were obtained in excellent yields and stereoselectivities, and a concise and large-scale synthesis of brivaracetam was developed from inexpensive L-2-aminobutyric acid. Surprisingly, stereodivergent hydrogenation was observed by modifying remote functionalized stereocenters and additives, which would provide alternative stereochemical options of chiral racetams synthesis.
引用
收藏
页码：2426 / 2431
页数：6
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