Tetrahedron

A new access to substituted tetraethyl N-Boc 2-aminoethylidene-1, 1-bisphosphonates and phosphonyl-substituted aza-Morita–Baylis–Hillman-type adducts

A Gajda, T Gajda

Index: Gajda, Anna; Gajda, Tadeusz Tetrahedron, 2008 , vol. 64, # 7 p. 1233 - 1241

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Citation Number: 33

Abstract

A general one-pot synthesis of substituted 2-aminoethylidene-1, 1-bisphosphonates has been developed. The protocol involves base-induced addition of sodium tetraethyl methylenebisphosphonate to N-Boc imines generated in situ from N-Boc-α-amidoalkyl-p- tolylsulfones by the action of sodium hydride. The direct and efficient conversion of the title compounds into aza-Morita–Baylis–Hillman-type adducts has been also elaborated.