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Highly diastereoselective conjugate addition of nitroalkanes to alpha,beta-unsaturated sugar lactones for the efficient synthesis of chiral 2-pyrrolidones
Li, Yan-Ping; Li, Zhong-Jun; Meng, Xiang-Bao
关键词Chiral 2-pyrrolidones Sugar Lactone Asymmetric Michael Addition Nitroalkane
刊名CARBOHYDRATE RESEARCH
2011-09-27
DOI10.1016/j.carres.2011.06.010
346期:13页:1801-1808
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Biochemistry & Molecular Biology ; Chemistry, Applied ; Chemistry, Organic
资助者Ministry of Science and Technology of China ; National Natural Science Foundation of China (NSFC) ; Ministry of Science and Technology of China ; National Natural Science Foundation of China (NSFC)
研究领域[WOS]Biochemistry & Molecular Biology ; Chemistry
关键词[WOS]GAMMA-LACTAMS ; PYRIDINIUM CHLOROCHROMATE ; ABSOLUTE-CONFIGURATION ; HYDROXAMIC ACIDS ; AMINO-ACIDS ; CYCLIZATION ; GLYCALS ; ROUTE ; ESTER
英文摘要

A series of 4,5-substituted chiral gamma-lactams were synthesized through a highly diastereoselective addition-rearrangement approach from 2,3-unsaturated sugar lactones. The single-crystal X-ray structure of one product indicated that the sugar ring was attacked from the axial side. Partial reduction of the nitro group produced N-hydroxy-gamma-lactams, which were further reduced with TiCl3 to yield the 4,5-substituted chiral gamma-lactams. The absolute configuration of C5 of the gamma-lactam was determined by NOESY spectra. (C) 2011 Elsevier Ltd. All rights reserved.

语种英语
所属项目编号2009ZX09501-011 ; 20602001
资助者Ministry of Science and Technology of China ; National Natural Science Foundation of China (NSFC) ; Ministry of Science and Technology of China ; National Natural Science Foundation of China (NSFC)
WOS记录号WOS:000300551700018
引用统计
被引频次:7[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/52295
专题北京大学药学院_化学生物学系
作者单位Peking Univ, State Key Lab Nat & Biomimet Drugs, Dept Biol Chem, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Li, Yan-Ping,Li, Zhong-Jun,Meng, Xiang-Bao. Highly diastereoselective conjugate addition of nitroalkanes to alpha,beta-unsaturated sugar lactones for the efficient synthesis of chiral 2-pyrrolidones[J]. CARBOHYDRATE RESEARCH,2011,346(13):1801-1808.
APA Li, Yan-Ping,Li, Zhong-Jun,&Meng, Xiang-Bao.(2011).Highly diastereoselective conjugate addition of nitroalkanes to alpha,beta-unsaturated sugar lactones for the efficient synthesis of chiral 2-pyrrolidones.CARBOHYDRATE RESEARCH,346(13),1801-1808.
MLA Li, Yan-Ping,et al."Highly diastereoselective conjugate addition of nitroalkanes to alpha,beta-unsaturated sugar lactones for the efficient synthesis of chiral 2-pyrrolidones".CARBOHYDRATE RESEARCH 346.13(2011):1801-1808.
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