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Synthesis 1988; 1988(6): 472-474
DOI: 10.1055/s-1988-27610
DOI: 10.1055/s-1988-27610
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Studies on Organophosphorus Compounds XXVIII. An Improved Synthetic Route to 1-Amino-Substituted Benzyl Phosphonic and -Phosphinic Acids
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Publication Date:
20 August 2002 (online)
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An improved method for the synthesis of 1-aminosubstituted benzyl phosphonic and -phosphinic acids under mild conditions is described. It consists of the reaction of diphenoxy chlorophosphine (1) or dichlorophenylphosphine (6) with substituted benzaldehydes 2 and a phosphoramidate 3 in the presence of a Lewis acid, followed by selective cleavage of the protective group of the resultant 1-(phosphorylamino)-substituted benzylphosphonate 4 or phosphinate 7, 9. A tentative reaction mechanism is postulated.