Synthesis 2013; 45(2): 193-198
DOI: 10.1055/s-0032-1317894
paper
© Georg Thieme Verlag Stuttgart · New York

Michael Addition of N-Heteroaromatics to Vinylphosphonates and Synthesis of Phosphoryl Pyrrolizones by Cyclization of Michael Adducts

Dilek Isik Tasgin
Hacettepe University, Department of Chemistry, 06800 Ankara, Turkey   Fax: +90(312)2992163   Email: canan@hacettepe.edu.tr
,
Canan Unaleroglu*
Hacettepe University, Department of Chemistry, 06800 Ankara, Turkey   Fax: +90(312)2992163   Email: canan@hacettepe.edu.tr
› Author Affiliations
Further Information

Publication History

Received: 19 October 2012

Received after revision: 22 November 2012

Publication Date:
07 December 2012 (online)


Abstract

Novel phosphonate compounds were synthesized via Michael addition of N-heteroaromatic compounds to aryl- and alkyl­-substituted vinylphosphonates using scandium triflate as the catalyst. Intramolecular cyclization reaction of the Michael adducts obtained gives novel (dimethoxyphosphoryl)pyrrolizin-3-ones in high yields as a single diastereomer.

Supporting Information

 
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