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Synthesis 2013; 45(2): 193-198
DOI: 10.1055/s-0032-1317894
DOI: 10.1055/s-0032-1317894
paper
Michael Addition of N-Heteroaromatics to Vinylphosphonates and Synthesis of Phosphoryl Pyrrolizones by Cyclization of Michael Adducts
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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.
Key words
phosphonates - pyrrolizinones - Michael addition - metal triflates - heteroaromatic compoundsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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