Science of Synthesis

Yamashita, M., Science of Synthesis, (2007) 30, 649.

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 N—C—P bond system. The most popular method for preparing N,P-acetals is the addition reaction of a P—H 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 N—C—P 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]

M,M-Meeeeee eee eeeeeeeee eeeeeeee ee eeeeeeeeee eeee eeeeeeeee ee α-eeeeeeeeeeeeeee eeeee. Meeee eeeeeeee eeeeeeeeee eeeeeeeeee eee eeeee eee ee eeeeeeeeee eeeeeee eeee eeeee eeeee eeeeeeeeee, eee eeeeeee, eeeeeeeee, eeeeeeeeee, eeeeeeeeeee, eee eeeeeeeee eeeeeeee eee eeeee eeee eee eeeeeeeeee eeeeeeee M,M-eeeeeee ee eee eeeeeee eee eeeeeeeee eeeeeeeee eeeeee ee eeeeeeeee.

Mee eee eeeeeeeeeee ee 8-eeeeeeeeeeeeeeeeeeee eeeee eee/ee 8-eeeeeeeeeeeeeeeeeeeeee, ee 8-eeeeeeeeeeeeeeeeeeee eeeee eee/ee 8-eeeeeeeeeeeeeeeeeeeeee, M—M, M—M, eee M—M eeee-eeeeeeeee eeeeeeeee eee eeee ee eee eeeeeeeee eeeeeeeeeee eeeee. Meeee eeee, M—M eeee-eeeeeeeee eeeeeeeee eee eeeeeeee eee eeee eeeeeeeeee eeee.[‌8‌]

References