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学科主题: 生命有机化学
题名: Studies on the synthesis of (2S,3R)-3-hydroxy-3-methylproline via C2-N bond formation
其他题名: 通过C2-N键形成的(2S,3R)-3-羟基-3-甲基脯氨酸的合成研究
作者: Shen JW(沈军伟) ; Qin DG(秦冬光) ; Zhang HW(张洪旺) ; Yao ZJ(姚祝军)
通讯作者: 姚祝军
刊名: J. Org. Chem.
发表日期: 2003-01-01
卷: 68, 期:19, 页:7479-7484
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所生命有机化学实验室
英文摘要: A new efficient synthesis of (2S,3R)-3-hydroxy-3-methylproline (3) is reported. During the course of a recent study on the lewis acid promoted intramolecular opening of an epoxide by a carbamate NH, a highly concerted rearrangement was unexpectedly obsered. Further investigations of substrate generality show the δ-carbamate-α,β-epoxide esters commonly underwent similar rearrangements with the aid of Lewis acids. Retrosynthetic analysis of such a C^2-N disconnection can lead to an efficient synthesis of (2S,#R)-3-hydroxy-3-methylproline (3) in high enantio purity. Stereochemistries were established by a sharpless asymmetric dihydroxylation and a diastereoselective reductive amination.
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/21043
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
Shen JW,Qin DG,Zhang HW,et al. Studies on the synthesis of (2S,3R)-3-hydroxy-3-methylproline via C2-N bond formation[J]. J. Org. Chem.,2003,68(19):7479-7484.
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