Synthesis 2008(18): 2986-2990  
DOI: 10.1055/s-2008-1067247
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Sulfinimine-Mediated Asymmetric Synthesis of Acyclic and Cyclic α-Aminophosphonates

Qianyi Chen, Jinfeng Li, Chengye Yuan*
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(21)54925379; e-Mail: yuancy@mail.sioc.ac.cn.;
Further Information

Publication History

Received 14 May 2008
Publication Date:
04 September 2008 (online)

Abstract

Nucleophilic addition of dialkylphosphites to N-tert-butanesufinimines proceeds smoothly at room temperature in the presence of potassium carbonate or potassium fluoride, affording acyclic α-alkyl-α-aminophosphonates and a series of cyclic α-aminophosphonates in good chemical yields and modest to high diastereoselectivities.