Kabachnik–Fields reaction: Difference between revisions
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The [[Kabachnik-Fields Reaction]] is an [[organic reaction]] forming an α-[[amino]] [[phosphonate]] from an [[amine]], a [[carbonyl]] compound and a [[dialkyl phosphite]]. Aminophosphonates are synthetic targets of some importance as [[phosphorus]] analogues of α-[[amino acid]]s (a [[bioisosterism|bioisosteric]]). This [[multicomponent reaction]] was independently discovered by |
The [[Kabachnik-Fields Reaction]] is an [[organic reaction]] forming an α-[[amino]] [[phosphonate]] from an [[amine]], a [[carbonyl]] compound and a [[dialkyl phosphite]]. Aminophosphonates are synthetic targets of some importance as [[phosphorus]] analogues of α-[[amino acid]]s (a [[bioisosterism|bioisosteric]]). This [[multicomponent reaction]] was independently discovered by [[Martin Izrailevich Kabachnik]] <ref>Kabachnik, M. I.; Medved, T. Ya. Dokl. Akad. Nauk SSSR '''1952'''</ref> and [[Ellis K. Fields]] <ref>''The Synthesis of Esters of Substituted Amino Phosphonic Acids'' Ellis K. Fields [[J. Am. Chem. Soc.]], '''1952''', 74 (6), pp 1528–1531 {{DOI|10.1021/ja01126a054}}</ref> in 1952. |
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:[[Image:Kabachnik-Fields Reaction.svg|Kabachnik-Fields Reaction]] |
:[[Image:Kabachnik-Fields Reaction.svg|Kabachnik-Fields Reaction]] |
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Revision as of 18:23, 20 March 2009
The Kabachnik-Fields Reaction is an organic reaction forming an α-amino phosphonate from an amine, a carbonyl compound and a dialkyl phosphite. Aminophosphonates are synthetic targets of some importance as phosphorus analogues of α-amino acids (a bioisosteric). This multicomponent reaction was independently discovered by Martin Izrailevich Kabachnik [1] and Ellis K. Fields [2] in 1952.
The first step in this reaction is the formation of an imine followed by an addition reaction of the phosphonate P-H bond into the C=N double bond (a Pudovik reaction) [3]. A related reaction is the Mannich reaction.
The reaction is accelerated with a combination of dehydrating reagent and Lewis acid. The carbonyl component in the reaction is usually an aldehyde and sometimes a ketone.
references
- ^ Kabachnik, M. I.; Medved, T. Ya. Dokl. Akad. Nauk SSSR 1952
- ^ The Synthesis of Esters of Substituted Amino Phosphonic Acids Ellis K. Fields J. Am. Chem. Soc., 1952, 74 (6), pp 1528–1531 doi:10.1021/ja01126a054
- ^ Catalytic Kabachnik-Fields reaction: new horizons for old reaction Nikolay S. Zefirov and Elena D. Matveeva ARKIVOC 2008 (i) 1-17 Link