期刊
TETRAHEDRON
卷 65, 期 41, 页码 8587-8595出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.07.040
关键词
Aminophosphonic acids; Heterocycles; Serine analogues; Nucleophilic addition; Piperidines
The synthesis of 2-hydroxy-4-heterocyclic phosphonic acids was achieved in a six-step sequence from the appropriate ketones. Thus, 2-hydroxyheterocyclic ketone acetals were prepared and then esterified by N-BoC-L-phenylalanine, used as a chiral auxiliary. The resulting heterocyclic acetal esters gave by a one-pot reaction bicyclic ketimines. These imines underwent nucleophilic addition with phosphite to provide efficiently and stereoselectively, under kinetic control, bicyclic aminophosphonates. Cleavage of the phenylalanine moiety by oxidation followed by acidic hydrolysis of the resulting hetero-cyclohexylphosphonates provided the new (4-amino-3-hydroxypiperidin-4-yl)-, (4-amino-3-hydroxytetrahydro-2H-pyran-4-yl)- and (1-amino-2-hydroxycyclohexyl)phosphonic acids. (C) 2009 Elsevier Ltd. All rights reserved.
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