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

Full Text: HTML

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.

Related Articles:

Preparation of new Wittig reagents and their application to the synthesis of α, β-unsaturated phosphonates

[Xu, Yuanyao; Jin, Xiaoli; Huang, Guohua; Huang, Yaozeng Synthesis, 1983 , # 7 p. 556 - 558]

Tetraarylphosphonium Halides as Arylating Reagents in Pd??Catalyzed Heck and Cross??Coupling Reactions

[Hwang, Lee Kyoung; Na, Youngim; Lee, Junseong; Do, Youngkyu; Chang, Sukbok Angewandte Chemie - International Edition, 2005 , vol. 44, # 38 p. 6166 - 6169]

Metallo-phosphorylation of alkynes: reaction of alkynes with Cp 2 Zr (1-butene)(PR 3) and chlorophosphate

[Lai, Chunbo; Xi, Chanjuan; Chen, Chao; Ma, Mingming; Hong, Xiaoyin Chemical Communications, 2003 , # 21 p. 2736 - 2737]

Stereoselective synthesis of vinylphosphonate

[Hirao, Toshikazu; Masunaga, Toshio; Ohshiro, Yoshiki; Agawa, Toshio Tetrahedron Letters, 1980 , vol. 21, # 37 p. 3595 - 3598]

Synthesis of diprotected monosubstituted hydrazine derivatives from tert-butyl carbazates and boronic acids

[Kabalka, George W.; Guchhait, Sankar K. Organic Letters, 2003 , vol. 5, # 5 p. 729 - 731]

More Articles...