Kabachnik-Fields reaction, review

The Kabachnik-Fields reaction is the three-component condensation of an aldehyde or ketone, an amine (secondary, primary, or ammonia) and a monobasic phosphorus(III) acid to yield an a-amino organophosphorus compound (a phos-phonate, phosphinate, or tertiary phosphine oxide) Scheme 28. It was discovered independently in 1952 by Kabachnik and Medved 120 and Fields,121 and may be regarded as a variant of the Pudovik reaction (Section 6), which was discovered contemporarily. The yields of the reaction tend to be only moderate (cf. Section 6), and are generally unsatisfactory with phosphinate reactants, but it is wide in scope and simple to perform. For a recent review of the Kabachnik-Fields reaction, including discussion of the mechanism (which usually proceeds via the imine), see Ref. 102. 

Since Kabachnik-Fields reaction and its synthetic applications have been intensively reviewed [147, 149, 153], herein, only some important examples developed in the last years will be shown. 

It worth to mention that despite the importance of the Kabachnik-Fields reaction, stereoselective versions for the synthesis of enantioenriched a-aminophosphonates are scarce [212, 213], and only few enantioselective examples have been published to date (for reviews on enantioselective catalytic direct hydrophosphonylations of imines, see Refs. [162a-c]). Organocatalytic examples use well-known chiral binol-derived phosphoric acid organocatalysts (Fig. 12.6,80 and 81) [214], and regarding metal catalysis, chiral scandium(III)-A,A -dioxide and... 

Scheme 52). Cherkasov et ah also studied the bis(Kabachnik-Fields) reaction and recent results of the Kabachnik-Fields reaction including the preparation of a-aminophosphine oxides have been reviewed. p-Aminophosphine oxides were obtained by the addition of primary and secondary amines to diphenyl(vinyl)phosphine oxide in water as the reaction medium (Scheme 53). ... 

The Kabachnik-Fields (phospha-Mannich) reaction has been reviewed, including evidence for imine intermediates via in situ FT-IR studies. Solvent-free microwave conditions are particularly effective, with little call for catalysts. 

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See also in sourсe #XX -- [ ]

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