A novel procedure for conversion of epoxides to α-hydroxyphosphonates with a trialkylphosphite mediated by LiClO4

被引:10
作者
Azizi, N [1 ]
Said, MR [1 ]
机构
[1] Sharif Univ Technol, Dept Chem, Tehran, Iran
关键词
epoxide; alpha-hydroxypliosphonates; trialkylphosphite; lithium perchlorate;
D O I
10.1016/j.tetlet.2003.09.002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method has been developed for the direct conversion of epoxides to alpha-hydroxyphosphonates by the reaction of a trialkylphosphite with the epoxide in 5 M lithium perchlorate in diethyl ether (LPDE). The reaction is highly regioselective and efficient with excellent yields under mild and neutral conditions. (C) 2003 Published by Elsevier Ltd.
引用
收藏
页码:7933 / 7935
页数:3
相关论文
共 27 条
[1]   Synthesis of tertiary α-amino phosphonate by one-pot three-component coupling mediated by LPDE [J].
Azizi, N ;
Saidi, MR .
TETRAHEDRON, 2003, 59 (28) :5329-5332
[2]   Lithium perchlorate diethyl ether solution: A highly efficient media for the Abramov reaction [J].
Azizi, N ;
Saidi, MR .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (06) :1255-1259
[3]   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
[4]   InBr3-catalyzed friedel-crafts addition of indoles to chiral aromatic epoxides:: A facile route to enantiopure indolyl derivatives [J].
Bandini, M ;
Cozzi, PG ;
Melchiorre, P ;
Umani-Ronchi, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5386-5389
[5]   Construction of tetrahydrofuran-3-ones from readily available organochalcogen precursors via radical carbonylation/reductive cyclization [J].
Berlin, S ;
Ericsson, C ;
Engman, L .
ORGANIC LETTERS, 2002, 4 (01) :3-6
[6]   PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES [J].
ENGEL, R .
CHEMICAL REVIEWS, 1977, 77 (03) :349-367
[7]   GENERAL SYNTHESIS OF 1-ALKYL-1-CYCLOPENTENE-CIS-3,5-DIOLS - USEFUL INTERMEDIATES IN PROSTAGLANDIN SYNTHESIS [J].
EVANS, DA ;
CRAWFORD, TC ;
FUJIMOTO, TT ;
THOMAS, RC .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (21) :3176-3178
[8]   Synthesis of phosphonates by nucleophilic substitution at phosphorus:: The SNP(V) reaction. [J].
Eymery, F ;
Iorga, B ;
Savignac, P .
TETRAHEDRON, 1999, 55 (46) :13109-13150
[9]   High yield preparation of a-ketophosphonates by oxidation of α-hydroxyphosphonates with zinc dichromate trihydrate (ZnCr2O7•3H2O) under solvent-free conditions [J].
Firouzabadi, H ;
Iranpoor, N ;
Sobhani, S ;
Sardarian, AR .
TETRAHEDRON LETTERS, 2001, 42 (26) :4369-4371
[10]  
Gröger H, 2000, CHEM-EUR J, V6, P943