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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