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Synthesis 2009(16): 2737-2740  
DOI: 10.1055/s-0029-1216877
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel Diastereoselective Synthesis of β-Phosphonato Unsaturated Thioimidates

Abdolali Alizadeh*, Nasrin Zohreh
Department of Chemistry, Tarbiat Modares University, P. O. Box 14115-175, Tehran 18716, Iran
Fax: +98(21)88006544; e-Mail: abdol_alizad@yahoo.com; e-Mail: aalizadeh@modares.ac.ir;
Further Information

Publication History

Received 14 April 2009
Publication Date:
26 June 2009 (online)

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Abstract

A novel, convenient, and efficient approach to the synthesis of α,β-unsaturated thioimidates with a phosphonate functional group in β-position has been reported based on a multicomponent reaction. The generated zwitterions from the reaction of trialkyl phosphites and dialkyl acetylenedicarboxylates are trapped with benzenecarbonyl isothiocyanate to produce the title compounds in good yield.

Key words

thioimidate - trialkyl phosphite - dialkyl acetylenedicarboxylate - benzenecarbonyl isothiocyanate - multicomponent reaction

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