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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
Zhang DH(张德晖); Yuan CY(袁承业)
2009
发表期刊Chem.-Eur. J.
ISSN0947-6539
卷号15期号:16页码:4088-4101
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.
学科领域元素有机化学
部门归属上海有机所
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收录类别SCI
语种英语
WOS记录号WOS:000265509700018
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被引频次:18[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/11080
专题上海有机化学研究所
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GB/T 7714
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.
APA 张德晖,&袁承业.(2009).Highly Enantioselective Synthesis of beta-Aminophosphinates with Two Stereogenic Atoms and Their Conversion into Optically Pure Ethyl beta-Amino-H-phosphinates.Chem.-Eur. J.,15(16),4088-4101.
MLA 张德晖,et al."Highly Enantioselective Synthesis of beta-Aminophosphinates with Two Stereogenic Atoms and Their Conversion into Optically Pure Ethyl beta-Amino-H-phosphinates".Chem.-Eur. J. 15.16(2009):4088-4101.
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