Diastereoselective synthesis of novel 5-substituted morpholine-3-phosphonic acids: further exploitation of N-acyliminium intermediates

作者：Bonilla Landa Israel; Luis Viveros Ceballos Jose; Ordonez Mario^*

来源：Tetrahedron: Asymmetry , 2014, 25(6-7): 485-487.

DOI：10.1016/j.tetasy.2014.02.014

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 BF3 center dot OEt2. Diastereoselectivity in the formation of cis-disubstituted products is in agreement with the nucleophilic addition to other methoxylated derivatives.

• 出版日期2014-4-15