Efficient regio- and stereoselective ring opening of epoxides with alcohols, acetic acid and water catalyzed by ammonium decatungstocerate(IV)

被引:82
作者
Mirkhani, V [1 ]
Tangestaninejad, S
Yadollahi, B
Alipanah, L
机构
[1] Isfahan Univ, Dept Chem, Esfahan 81746, Iran
[2] IASBS, Zanjan 45138, Iran
关键词
catalysis; ring opening; epoxides; alcohols; hydrolysis;
D O I
10.1016/j.tet.2003.08.018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Epoxides can be cleaved in a regio- and stereoselective manner under neutral conditions with alcohols and acetic acid in the presence of catalytic amounts of decatungstocerate(IV) ion, ([CeW10O36](8-)), affording the corresponding beta-alkoxy and beta-acetoxy alcohols in high yields. In water, ring opening of epoxides occurs with this catalyst to produce the corresponding diols in good yields. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8213 / 8218
页数:6
相关论文
共 40 条
[1]  
*ALDR CAT, 1990, HDB FIN CHEM
[2]  
CHINI M, 1992, SYNLETT, P673
[3]   LANTHANIDE(III) TRIFLUOROMETHANESULFONATES AS EXTRAORDINARILY EFFECTIVE NEW CATALYSTS FOR THE AMINOLYSIS OF 1,2-EPOXIDES [J].
CHINI, M ;
CROTTI, P ;
FAVERO, L ;
MACCHIA, F ;
PINESCHI, M .
TETRAHEDRON LETTERS, 1994, 35 (03) :433-436
[4]   HETEROPOLYTUNGSTATE COMPLEXES OF LANTHANOID ELEMENTS .3. CRYSTAL-STRUCTURE OF SODIUM DECATUNGSTOCERATE(IV)-WATER(1/30) [J].
IBALL, J ;
LOW, JN ;
WEAKLEY, TJR .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (18) :2021-2024
[5]   EFFICIENT, MILD, AND REGIOSELECTIVE CONVERSION OF THIIRANES TO ALKOXY AND ACETOXY DISULFIDES AND DITHIANES WITH CE(IV) BASED OXIDANTS [J].
IRANPOOR, N ;
OWJI, J .
TETRAHEDRON, 1991, 47 (01) :149-154
[6]  
Iranpoor N, 1996, SYNTHESIS-STUTTGART, P1473
[7]   Highly efficient, regio- and stereoselective ring opening of epoxides and thiiranes with Ce(OTf)4 [J].
Iranpoor, N ;
Shekarriz, M ;
Shiriny, F .
SYNTHETIC COMMUNICATIONS, 1998, 28 (02) :347-366
[8]   MILD, EFFICIENT AND SELECTIVE OPENING OF EPOXIDES WITH ALCOHOLS CATALYZED BY CERIC(IV) AMMONIUM-NITRATE [J].
IRANPOOR, N ;
BALTORK, IM .
SYNTHETIC COMMUNICATIONS, 1990, 20 (18) :2789-2797
[9]   CERIC AMMONIUM-NITRATE, AN EFFICIENT CATALYST FOR MILD AND SELECTIVE OPENING OF EPOXIDES IN THE PRESENCE OF WATER THIOLS AND ACETIC-ACID [J].
IRANPOOR, N ;
BALTORK, IM ;
ZARDALOO, FS .
TETRAHEDRON, 1991, 47 (47) :9861-9866
[10]   2,3-DICHLORO-5,6-DICYANO-PARA-BENZOQUINONE, AN EFFICIENT, MILD, NEUTRAL AND HIGHLY REGIOSELECTIVE CATALYST FOR ALCOHOLYSIS OF EPOXIDES [J].
IRANPOOR, N ;
BALTORK, IM .
TETRAHEDRON LETTERS, 1990, 31 (05) :735-738