1.1-(Alpha-aminobenzyl)-2-naphthol: a new chiral auxiliary for the synthesis of enantiopure alpha-aminophosphonic acids.
Metlushka KE1, Kashemirov BA, Zheltukhin VF, Sadkova DN, Büchner B, Hess C, Kataeva ON, McKenna CE, Alfonsov VA. Chemistry. 2009 Jul 6;15(27):6718-22. doi: 10.1002/chem.200802540.
A new diastereoselective synthesis of alpha-aminophosphonates has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(alpha-aminobenzyl)-2-naphthol. The reaction proceeds at room temperature in toluene with high diastereoselectivity. The major diastereomer can be separated by crystallization from an appropriate solvent. The relative configuration of both chiral centers of the major diastereomer was determined by single-crystal X-ray structure analysis. The desired alpha-aminophosphonic acids can be obtained in enantiopure form by treatment of the corresponding diastereomers with HCl.