Highly stereoselective synthesis of new α-amino-β-hydroxy six-membered heterocyclic phosphonic acids, serine analogues

N Louaisil, N Rabasso, A Fadel

Index: Louaisil, Nicolas; Rabasso, Nicolas; Fadel, Antoine Tetrahedron, 2009 , vol. 65, # 41 p. 8587 - 8595

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Citation Number: 13

Abstract

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 ...