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首页> 外文期刊>Chemistry: A European journal >Highly Enantioselective Synthesis of beta-Aminophosphinates with Two Stereogenic Atoms and Their Conversion into Optically Pure Ethyl beta-Amino-H-phosphinates
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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

机译：具有两个立体原子的β-氨基次膦酸酯的高对映选择性合成及其转化为光学纯的β-氨基-H次膦酸酯

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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.
机译：（1,1-二乙氧基乙基）甲基次膦酸乙酯和nBuLi在-S-N-（叔丁烷亚磺酰基）亚胺上于-78℃对阴离子进行亲核攻击，实现了β-氨基次膦酸酯的第一个高度立体选择性合成。随后通过关键的金属催化的硫代酚解作用除去保护基团，产生光学上纯的β-氨基-H-次膦酸乙酯。在该过程中，可以获得在磷原子上具有不同构型的一对非对映异构体。迄今为止，Ellman N-（叔丁烷亚磺酰基）亚胺在α-氨基次膦酸酯和β-氨基次膦酸酯的合成中均表现出优异的手性诱导活性。另一方面，Cram规则已成功应用于合理化（RC）-α-氨基次膦酸酯和（RC）-β-氨基次膦酸酯的高对映选择性形成，而两对非对映异构体都可以被有效分离的现象是基于X射线晶体结晶和H-1 NMR光谱分析进行了初步讨论。

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