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30.7.1 Product Subclass 1: N,P-Acetals

DOI: 10.1055/sos-SD-030-00514

Yamashita, M.Science of Synthesis, (200730649.

General Introduction

As phosphorus analogues of natural α-amino acids, 1-aminoalkylphosphonic acids (α-aminophosphonic acids) and their derivatives have attracted wide attention in synthetic chemistry, biochemistry, medicinal chemistry, medicine, and the agricultural sciences. Compounds such as 1-aminoalkylphosphonic acids are categorized here as N,P-acetals, as they have a NCP bond system. The most popular method for preparing N,P-acetals is the addition reaction of a PH group of a phosphorus compound such as a dialkyl phosphonate [dialkyl phosphite, (R1O)2P(O)H] to a C=N bond (the hydrophosphonation reaction, and modified versions thereof) to prepare the NCP linkage. This section summarizes reported methods for preparing 1-aminoalkylphosphonates (and related phosphorus derivatives such as phosphinates), including stereoselective reactions to prepare chiral 1-aminoalkylphosphonates derivatives, which are attractive targets with a wide range of biological properties such as antibiotic, enzyme-inhibitor, and herbicide activities.[‌1‌] For example, 1-(alkoxycarbonyl)aziridin-2-ylphosphonic acid, an aziridine analogue of fosfomycin, a broad-spectrum clinically used antibiotic that is itself an oxirane derivative of a phosphonic acid, also shows antibacterial activity. The synthesis of related cyclic phosphonates is reported in the patent literature.[‌2‌]

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