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 phosphonate. Aminophosphonates are synthetic targets of some importance as [[phosphorus]] analogues of α-[[amino acid]]s (a [[bioisosterism|bioisostere]]). This [[multicomponent reaction]] was independently discovered by [[Martin Izrailevich Kabachnik]]<ref>{{cite journal| last=Kabachnik | first=Martin I. |author2=T. Ya. Medved | year=1952 | title=Новый метод синтеза сс-аминофосфиновых кислот | trans_title=<!-- A new method for the synthesis of α-amino ? acids --> | journal=[[Doklady Akademii Nauk SSSR]] | volume=83 | page=689}}</ref> and [[Ellis K. Fields]]<ref>{{cite journal| last=Fields | first=Ellis K. | year=1952 | title=The synthesis of esters of substituted amino phosphonic acids | journal=[[Journal of the American Chemical Society]] | volume=74 | issue=6 | pages=1528–1531 | doi=10.1021/ja01126a054}}</ref> in 1952. |
The '''Kabachnik–Fields reaction''' is an [[organic reaction]] forming an α-[[amino]] [[phosphonate]] from an [[amine]], a [[carbonyl]] compound and a [[diethylphosphite|dialkyl phosphonate]] ((RO)2P(O)H). Aminophosphonates are synthetic targets of some importance as [[phosphorus]] analogues of α-[[amino acid]]s (a [[bioisosterism|bioisostere]]). This [[multicomponent reaction]] was independently discovered by [[Martin Izrailevich Kabachnik]]<ref>{{cite journal| last=Kabachnik | first=Martin I. |author2=T. Ya. Medved | year=1952 | title=Новый метод синтеза сс-аминофосфиновых кислот | trans_title=<!-- A new method for the synthesis of α-amino ? acids --> | journal=[[Doklady Akademii Nauk SSSR]] | volume=83 | page=689}}</ref> and [[Ellis K. Fields]]<ref>{{cite journal| last=Fields | first=Ellis K. | year=1952 | title=The synthesis of esters of substituted amino phosphonic acids | journal=[[Journal of the American Chemical Society]] | volume=74 | issue=6 | pages=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 13:41, 7 July 2017
The Kabachnik–Fields reaction is an organic reaction forming an α-amino phosphonate from an amine, a carbonyl compound and a dialkyl phosphonate ((RO)2P(O)H). Aminophosphonates are synthetic targets of some importance as phosphorus analogues of α-amino acids (a bioisostere). 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, Martin I.; T. Ya. Medved (1952). "Новый метод синтеза сс-аминофосфиновых кислот". Doklady Akademii Nauk SSSR. 83: 689.
{{cite journal}}: Cite has empty unknown parameter:|trans_title=(help) - ^ Fields, Ellis K. (1952). "The synthesis of esters of substituted amino phosphonic acids". Journal of the American Chemical Society. 74 (6): 1528–1531. doi:10.1021/ja01126a054.
- ^ Zefirov, Nikolay S.; Elena D. Matveeva (2008-01-18). "Catalytic Kabachnik-Fields reaction: New horizons for old reaction" (PDF). ARKIVOC. 2008 (i): 1–17. doi:10.3998/ark.5550190.0009.101. Retrieved 2009-12-08.