1-(alpha-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure alpha-Aminophosphonic Acids

Metlushka KE; Kashemirov BA; Zheltukhin VE; Sadkova DN; Buchner B; Hess C; Kataeva ON; McKenna CE; Alfonsov VA

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1-(alpha-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure alpha-Aminophosphonic Acids

机译：1-（α-氨基苄基）-2-萘酚：合成对映体纯α-氨基膦酸的新型手性助剂

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摘要

A new diastereoselective synthesis of alpha-aminophosphonates has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(alpha-aminobenzyl)-2-naphthol. The reaction proceeds at room temperature in toluene with high diastereoselectivity. The major diastereomer can be separated by crystallization from an appropriate solvent. The relative configuration of both chiral centers of the major diastereomer was determined by single-crystal X-ray structure analysis. The desired alpha-aminophosphonic acids can be obtained in enantiopure form by treatment of the corresponding diastereomers with HCl.

机译：基于在三氟乙酸存在下，亚磷酸三烷基酯与衍生自（R）-或（S）-1-（α-氨基苄基）-2的手性亚胺的反应，已经开发了一种新的非对映选择性合成α-氨基膦酸酯的方法。 -萘酚。反应在室温下在甲苯中以高非对映选择性进行。可以通过从适当的溶剂中结晶来分离主要的非对映异构体。主要的非对映异构体的两个手性中心的相对构型是通过单晶X射线结构分析确定的。所需的α-氨基膦酸可以通过用HCl处理相应的非对映异构体而以对映纯的形式获得。

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《Chemistry: A European journal》 |2009年第27期|共5页
作者
Metlushka KE; Kashemirov BA; Zheltukhin VE; Sadkova DN; Buchner B; Hess C; Kataeva ON; McKenna CE; Alfonsov VA;
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正文语种 eng
中图分类应用化学;
关键词
aminophosphonic acids; asymmetric synthesis; Betti bases; chiral auxiliaries; imines;

机译：氨基膦酸;不对称合成;贝蒂碱;手性助剂;亚胺;

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1. 1-(alpha-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure alpha-Aminophosphonic Acids [J] . Metlushka KE, Kashemirov BA, Zheltukhin VE, Chemistry: A European journal . 2009,第27期

机译：1-（α-氨基苄基）-2-萘酚：合成对映体纯α-氨基膦酸的新型手性助剂
2. Diastereoselective Synthesis of Enantiopure Cyclic alpha-Aminophosphonic Acids [J] . Alfonsov VA, McKenna CE, Bayandina EV, Phosphorus, Sulfur, and Silicon and the Related Elements . 2008,第11期

机译：对映纯环状α-氨基膦酸的非对映选择性合成
3. A new efficient procedure for asymmetric synthesis of alpha-aminophosphonic acids via addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure sulfinimines [J] . Mikolajczyk M., Lyzwa P., Drabowicz J. Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2002,第23期

机译：通过将锂化的双（二乙基氨基）膦硼烷络合物添加到对映纯的亚磺胺中，可以有效地不对称合成α-氨基膦酸的新方法
4. Simulation-Based Optimization of Bi-Enzymatic System for the Synthesis of Enantiopure Chiral Compounds [C] . BOGALE TADESS FANTAYE, IJAZ GUL, LIXIA TANG International Computer Conference on Wavelet Active Media Technology and Information Processing . 2019

机译：基于模拟的双酶体系优化对映纯手性化合物的合成
5. Applications of enantiopure sulfinimine derived chiral amine building blocks for the asymmetric synthesis of tropane alkaloids and cyclic cis-β-amino acid derivatives [D] . Theddu, Naresh 2011

机译：对映体纯的亚氨嘧啶衍生的手性胺结构单元在托烷生物碱和环状顺式-β-氨基酸衍生物的不对称合成中的应用
6. Enhanced Stereoselectivity of a Cu(II) Complex Chiral Auxiliary in the Synthesis of Fmoc-L-γ-carboxyglutamic Acid [O] . Daniel J. Smith, Glenn P. A. Yap, James A. Kelley, -1

机译：增强Cu（II）复合手性助剂的立体选择性在合成FMOC-L-γ-羧基酸的合成中
7. 1-(2, 4, 6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of g-Amino Acid Derivatives [O] . -1

机译：1-（2,4,6-三异丙基苯基）乙胺：用于非对称合成G-氨基酸衍生物的新的手性助剂

1-(alpha-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure alpha-Aminophosphonic Acids

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