CHIRAL SYMMETRICAL PHOSPHORIC-ACID ESTERS AS SOURCES OF OPTICALLY-ACTIVE ORGANOPHOSPHORUS COMPOUNDS

Chiral symmetric di- and trialkylphosphites, derivatives of (-)-borneo l, (-)-menthol and 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose, were studied as starting reagents for the preparation of chiral organo phosphorus compounds. The reaction occurs by asymmetric induction at t he alpha-carbon atom of substituted alpha-alkylphosphonates. The stere oselectivity of the reaction depends on the structure of the starting compounds and the reaction conditions. The configuration of the alkylp hosphonates was established by NMR spectroscopy, by transformation int o alpha-hydroxyalkylphosphonic acids and by X-ray crystal structure an alysis. (C) 1998 Elsevier Science Ltd. All rights reserved.