Synthesis of tertiary α-amino phosphonate by one-pot three-component coupling mediated by LPDE

被引:86
作者
Azizi, N [1 ]
Saidi, MR [1 ]
机构
[1] Sharif Univ Technol, Dept Chem, Tehran, Iran
关键词
tertiary alpha-amino phosphonate; trialkylphosphite; lithium perchlorate;
D O I
10.1016/S0040-4020(03)00759-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A very mild, efficient and simple method for the synthesis of tertiary alpha-amino phosphonates is reported by reaction of an aldehyde, a secondary amine and trialkylphosphite in ethereal solution of lithium perchlorate, LPDE, at ambient temperature with high yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5329 / 5332
页数:4
相关论文
共 23 条
[1]   β,γ-Unsaturated α-aminophosphonates:: synthesis and reactivity [J].
Atmani, A ;
Combret, JC ;
Malhiac, C ;
Mulengi, JK .
TETRAHEDRON LETTERS, 2000, 41 (32) :6045-6048
[2]   A new protocol for the Baylis-Hillman reaction: the reaction of iminium salts prepared in situ with methyl acrylate [J].
Azizi, N ;
Saidi, MR .
TETRAHEDRON LETTERS, 2002, 43 (24) :4305-4308
[3]  
BABUDRI F, 1991, SYNTHESIS-STUTTGART, P225
[4]   Three component coupling catalyzed by TaCl5-SiO2:: synthesis of α-amino phosphonates [J].
Chandrasekhar, S ;
Prakash, SJ ;
Jagadeshwar, V ;
Narsihmulu, C .
TETRAHEDRON LETTERS, 2001, 42 (32) :5561-5563
[5]   Asymmetric synthesis of alpha-aminophosphonates via diastereoselective addition of phosphite to chiral imine derivatives [J].
Chung, SK ;
Kang, DH .
TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :21-24
[6]  
ENGEL R, 1992, HDB ORGANOPHOSPHORUS, pCH7
[7]  
GERBER JP, 1994, PHOSPHORUS SULFUR, V88, P111
[8]   Lithium perchlorate/diethylether catalyzed aminophosphonation of aldehydes [J].
Heydari, A ;
Karimian, A ;
Ipaktschi, J .
TETRAHEDRON LETTERS, 1998, 39 (37) :6729-6732
[9]   PEPTIDE-SYNTHESIS CATALYZED BY AN ANTIBODY CONTAINING A BINDING-SITE FOR VARIABLE AMINO-ACIDS [J].
HIRSCHMANN, R ;
SMITH, AB ;
TAYLOR, CM ;
BENKOVIC, PA ;
TAYLOR, SD ;
YAGER, KM ;
SPRENGELER, PA ;
BENKOVIC, SJ .
SCIENCE, 1994, 265 (5169) :234-237
[10]   BIOLOGICAL-ACTIVITY OF AMINOPHOSPHONIC ACIDS [J].
KAFARSKI, P ;
LEJCZAK, B .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 63 (1-2) :193-215