Israel Bonilla-Landa, José Luis Viveros‐Ceballos, M. Ordóñez
Apr 15, 2014
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Journal
Tetrahedron-asymmetry
Abstract
Abstract The first diastereoselective total synthesis of 5-substituted morpholine-3-phosphonic acids is reported. The principal feature of the synthesis is the introduction of a dimethyl phosphonate group into 5-substituted morpholin-3-ones. The procedure is based on the preparation of N -Boc-( S )-5-phenyl- and N -Boc-( S )-5-benzylmorpholin-3-one from l -phenylglycine and l -phenylalanine methyl esters, followed by the formation of the 3-methoxylated compounds and subsequent reaction with trimethyl phosphite in the presence of BF 3 ·OEt 2 . Diastereoselectivity in the formation of cis -disubstituted products is in agreement with the nucleophilic addition to other methoxylated derivatives.