PRODUCTION OF OPTICALLY ACTIVE ALPHA-AMINOPHOSPHONIC ACID DERIVATIVE AND CATALYST FOR ASYMMETRIC SYNTHESIS AND NEW PHOSPHONATE-BASED COMPOUND

摘要

PURPOSE: To produce an optically active α-aminophosphonic acid derivative useful as an antimicrobial gent, etc., by reacting an imine with a phosphonic acid ester in the presence of a specific catalyst for asymmetric synthesis and then deprotecting and hydrolyzing the produced phosphonate compound by contact with an acid or hydrogen. ;CONSTITUTION: An imine of formula I (R¹ is trityl, benzyl or di-p-anisylmethyl; R² is an alkyl, a cycloalkyl, an aryl or a hydrocarbon containing an aryl group) is reacted with a phosphonic acid ester of formula II (R³ is an alkyl, a cycloalkyl, an allyl, an aryl, etc.) in the presence of a catalyst for asymmetric synthesis of the formula La-X-binaphthol (X is an alkali metal) to synthesize a phosphonate-based compound of formula III or IV, which is then brought into contact with an acid or hydrogen to carry out the deprotection or hydrolysis. Thereby, the objective optically active α-aminophosphonic acid derivative of formula V or VI, partially containing a new compound and having antimicrobial activities is efficiently obtained in a large amount.;COPYRIGHT: (C)1996,JPO