Journal of Organic Chemistry p. 3654 - 3658 (1987)
Update date:2022-08-04
Topics:
Calvo, Kim C.
The reaction between pyridoxal and α-amino phosphonic acids is reported.Under the proper conditions, the amino phosphonates can be induced to undergo a pyridoxal-promoted cleavage of the P-C bond.The reaction requires a metal ion and a phosphonic acid that possesses a chelating heteroatom in a position β to the amino group.At 100 deg C and pH 8.8, the dephosphonylation reaction is a first-order process, producing orthophosphate and an aldehyde from the amino phosphonate and pyridoxamine from the pyridoxal.The mechanism proposed for this reaction is based on an analogy with the pyridoxal-catalyzed decarboxylation of α-amino acids.The reactions reported represent the first observation of an α dephosphonylation mediated by pyridoxal.
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