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Synthesis 2009(8): 1227-1254
DOI: 10.1055/s-0028-1088031
DOI: 10.1055/s-0028-1088031
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
Michael Additions to Activated Vinylphosphonates
Further Information
Received
20 January 2009
Publication Date:
25 March 2009 (online)
Publication History
Publication Date:
25 March 2009 (online)
Abstract
Activated vinylphosphonates constitute a very important group of organic reagents which have found broad application in organic synthesis. The most important feature of activated vinylphosphonates is certainly their ability to undergo Michael additions in which a wide variety of carbo- and heteronucleophiles can be used. This review presents the potential of activated vinylphosphonates as Michael acceptors and shows possible applications of the thus-formed adducts, in particular as Horner-Wadsworth-Emmons olefinating reagents, in the synthesis of important carbo- and heterocycles as well as acyclic compounds. Selected preparations of activated vinylphosphonates are also described.
1 Introduction
2 Synthesis of Carbocyclic Compounds
3 Synthesis of Heterocyclic Compounds
4 Synthesis of Acyclic Compounds
4.1 Addition of Carbon Nucleophiles Followed by HWE Olefination
4.2 Addition of Carbon Nucleophiles without Removal of the Phosphonate Group
4.3 Addition of Heteronucleophiles Followed by HWE Olefination
4.4 Addition of Heteronucleophiles without Removal of the Phosphonate Group
5 Concluding Remarks
Key words
activated vinylphosphonates - Michael additions - Wittig type reactions - carbocycles - heterocycles
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References
The reference was cited as: Monguchi, D.; Furuta, T.; Tanaka, K., manuscript in preparation.