Asymmetric Synthesis of β-Amino Phosphonate Derivatives throughNatural Amino Acids Derived α-Diazophosphonates

doi:10.6023/cjoc201504035

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2135-2141.DOI: 10.6023/cjoc201504035 Previous Articles Next Articles

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由氨基酸衍生α-重氮膦酸酯不对称合成β-氨基膦酸酯衍生物反应研究

胡辰飞^b, 蔡岩^a, 木尼热·阿布都克力木^c, 苗志伟^a,c

a 南开大学元素有机化学研究所天津 300071;
b 天津理工大学化学化工学院天津 300384;
c 喀什大学化学与环境科学学院新疆喀什 844006

收稿日期:2015-04-23 修回日期:2015-06-02 发布日期:2015-06-12
通讯作者: 木尼热·阿布都克力木, 苗志伟 E-mail:miaozhiwei@nankai.edu.cn
基金资助:
天津市自然科学基金(No. 15JCYBJC20700)和新疆特色药食用植物资源化学实验室开放课题(No. 2015KL030)资助项目.

Asymmetric Synthesis of β-Amino Phosphonate Derivatives throughNatural Amino Acids Derived α-Diazophosphonates

Hu Chenfei^b, Cai Yan^a, Munira·Abudukeremu^c, Miao Zhiwei^a,c

a Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071;
b School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384;
c College of Chemistry and Environmental Sciences, Kashgar University, Kashgar 844006

Received:2015-04-23 Revised:2015-06-02 Published:2015-06-12
Supported by:
Project supported by the Committee of Science and Technology of Tianjin City (No. 15JCYBJC20700) and the Xinjiang Laboratory of Native Medicinal and Edible Plant Resources Chemistry Open Subject (2015KL030).

1. Asymmetric Synthesis of β-Amino Phosphonate Derivatives throughNatural Amino Acids Derived α-Diazophosphonates.PDF(4115KB)

Abstract

An efficient procedure was developed for the asymmetric synthesis of (S)-diethyl (2-(1,3-dioxoisoindolin-2-yl)propyl)phosphonates employing (S)-diethyl (1-diazo-2-(1,3-dioxoisoindolin-2-yl)alkyl)phosphonates as starting materials. The reaction was catalyzed by 5% Pd/C and used glacial acetic acid as additive in i-PrOH as solvent. The obtained optical β-amino phosphonate derivatives were identified by ¹H NMR, ¹³C NMR, ³¹P NMR and HRMS and the enantiomeric excess was 95%. This process provided straightforward access to optical β-aminophosphonate derivatives in good yields with high stereoselectivities.

Key words: chiral induction, β-amino phosphonate, asymmetric synthesis, α-diazophosphonate

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Hu Chenfei, Cai Yan, Munira·Abudukeremu, Miao Zhiwei. Asymmetric Synthesis of β-Amino Phosphonate Derivatives throughNatural Amino Acids Derived α-Diazophosphonates[J]. Chin. J. Org. Chem., 2015, 35(10): 2135-2141.

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由氨基酸衍生α-重氮膦酸酯不对称合成β-氨基膦酸酯衍生物反应研究

Asymmetric Synthesis of β-Amino Phosphonate Derivatives throughNatural Amino Acids Derived α-Diazophosphonates

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