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Catalyst-Free and Selective C-N Bond Functionalization: Stereospecific Three-Component Coupling of Amines, Dichloromethane, and >P(O)H Species Affording α-Aminophosphorus Compounds

Yalei Zhao, Xiuling Chen, Tieqiao Chen, Yongbo Zhou*, Shuang-Feng Yin* and Li-Biao Han

*State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, People’s Republic of China, Email: zhouybhnu.edu.cn, sf_yinhnu.edu.cn

Y. Zhao, X. Chen, T. Chen, Y. Zhou, S.-F. Yin, L.-B. Han, J. Org. Chem., 2015, 80, 62-69.

DOI: 10.1021/jo501961h (free Supporting Information)


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Abstract

A three-component coupling of amines, dihalomethane, and >P(O)H species enables a catalyst-free and selective synthesis of various phosphorus analogues of α-amino acids. This reaction takes place stereospecifically with retention of configuration at phosphorus.

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Key Words

α-amino phosphonates


ID: J42-Y2015