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Synthesis 2009(23): 3930-3940  
DOI: 10.1055/s-0029-1217054
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Versatile and Highly Stereoselective Synthesis of Diethyl (1-Aminoalkyl)thiophosphonates

Zhilong Chen, Jinfeng Li, Chengye Yuan*
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-lin Rd, Shanghai, 200032, P. R. of China
Fax: +86(21)54925379; e-Mail: yuancy@mail.sioc.ac.cn;
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Publication History

Received 8 June 2009
Publication Date:
19 October 2009 (online)

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Abstract

A series of chiral diethyl (1-aminoalkyl)thiophosphonates was synthesized in high yield and excellent enantioselectivity by nucleophilic addition of diethyl thiophosphonate to N-(tert-butylsulfinyl)imines under mild conditions. There is no evidence indicating that the reaction is influenced by electronic or steric effects of the substrates.

Key words

nucleophilic additions - thiophosphonates - imines - sulfinamides - sulfonamides

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CCDC 727150 contains the supplementary crystallographic data of compound 6g. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.