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Synthesis 2008(7): 1085-1093  
DOI: 10.1055/s-2008-1032127
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile Synthesis of Chiral 4-(tert-Butylsulfinylamino)-2-oxophosphonates and Their Conversion into 5,5-Disubstituted 2-Benzylidene-3-oxopyrrolidines

Qianyi Chen, Chengye Yuan*
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences­, 354 Fenglin Lu, Shanghai 200032, P. R. of China
Fax: +86(21)54925379; e-Mail: yuancy@mail.sioc.ac.cn;
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Publication History

Received 26 September 2007
Publication Date:
06 March 2008 (online)

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Abstract

The addition of the dianion derived from 2-oxophosphonates to chiral N-(tert-butylsulfinyl)ketimines or -aldimine under mild reaction conditions afforded 4-(tert-butylsulfinylamino)-2-oxoalkylphosphonates with good to excellent diastereoselectivity. The latter was then converted into an enantiopure 5,5-disubstituted 2-(dimethoxyphosphoryl)pyrrolidin-3-one via an intramolecular N-H insertion. Subsequent Horner-Wadsworth-Emmons reaction gave the corresponding 2-benzylidene derivatives.

Key words

chiral N-substituted 4-amino-2-oxophosphonates - N-sulfinylimines - asymmetric-induced addition - pyrrolidinone - intramolecular N-H insertion - Horner-Wadsworth-Emmons reaction