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学科主题: 元素有机化学
题名: Highly Enantioselective Synthesis of beta-Aminophosphinates with Two Stereogenic Atoms and Their Conversion into Optically Pure Ethyl beta-Amino-H-phosphinates
其他题名: 首次高选择性合成带有两个手性中心的β-氨基次膦酸酯及其转化为光学纯的乙基β-氨基次膦酸
作者: Zhang DH(张德晖) ; Yuan CY(袁承业)
刊名: Chem.-Eur. J.
发表日期: 2009
卷: 15, 期:16, 页:4088-4101
收录类别: SCI
部门归属: 上海有机所
英文摘要: The first highly stereoselective synthesis of beta-aminophosphinates has been realized by the nucleophilic attack of an anion generated from ethyl (1,1-diethoxyethyl)methylphosphinate and nBuLi on (S)-N-(tert-butanesulfinyl)imines at -78 degrees C. Subsequent removal of the protecting groups through pivotal metal-catalyzed thiophenolysis leads to optically pure ethyl beta-amino-H-phosphinates. During this process, a pair of diastereoisomers with different configurations on the phosphorus atom can be obtained. Until now Ellman N-(tert-butanesulfinyl)imines have demonstrated excellent chirality-induced activity in the syntheses of both alpha-aminophosphinates and beta-aminophosphinates. On the other hand, the Cram rules have been successfully applied to rationalize the highly enantioselective formation of (R-C)-alpha-aminophosphinates and (R-C)-beta-aminophosphinates, whereas the phenomenon that the two pairs of diastereoisomers could both be efficiently isolated is tentatively discussed based on X-ray crystalloaraphic and H-1 NMR spectroscopic analysis.
语种: 英语
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WOS记录号: WOS:000265509700018
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/11080
Appears in Collections:上海有机化学研究所_期刊论文

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Recommended Citation:
Zhang DH,Yuan CY. Highly Enantioselective Synthesis of beta-Aminophosphinates with Two Stereogenic Atoms and Their Conversion into Optically Pure Ethyl beta-Amino-H-phosphinates[J]. Chem.-Eur. J.,2009,15(16):4088-4101.
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