Lewis-acid catalyzed organic reactions in water.: The case of AlCl3, TiCl4, and SnCl4 believed to be unusable in aqueous medium

被引：94

作者：

Fringuelli, F ^{[1
]}

Pizzo, F ^{[1
]}

Vaccaro, L ^{[1
]}

机构：

[1] Univ Perugia, Dipartimento Chim, I-06123 Perugia, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 13期

关键词：

D O I：

10.1021/jo010373y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Classical Lewis acids such as AlCl3, TiCl4, and SnCl4, believed to be unusable as catalysts in aqueous medium, efficiently catalyzed regio- and stereoselective azidolysis and iodolysis of alpha,beta -epoxycarboxylic acids in water at pH 4.0 and 1.5, respectively. The concept of water-tolerant metal-salt is reexamined in direct relationship to the aqua ion hydrolysis constant.

引用

页码：4719 / 4722

页数：4

共 23 条

[11] LANTHANIDE TRIFLATES AS WATER-TOLERANT LEWIS-ACIDS - ACTIVATION OF COMMERCIAL FORMALDEHYDE SOLUTION AND USE IN THE ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES IN AQUEOUS-MEDIA
KOBAYASHI, S
HACHIYA, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) : 3590 - 3596
[12] Laurent-Robert H, 1998, SYNLETT, P1138
[13] LEGTERS J, 1992, RECL TRAV CHIM PAY B, V111, P1
[14] Li C. -J., 1997, ORGANIC REACTIONS AQ
[15] A HIGHLY STEREOSELECTIVE CONVERSION OF ALPHA,BETA-EPOXY ESTERS TO ALPHA-HYDROXY ESTERS - AN EFFICIENT ROUTE TO OPTICALLY-ACTIVE ALPHA-HYDROXYESTERS
OTSUBO, K
INANAGA, J
YAMAGUCHI, M
[J]. TETRAHEDRON LETTERS, 1987, 28 (38) : 4435 - 4436
[16] Million-fold acceleration of a Diels-Alder reaction due to combined Lewis acid and micellar catalysis in water
Otto, S
Engberts, JBFN
Kwak, JCT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) : 9517 - 9525
[17] RICHENS DT, 1997, CH4EM AQUA IONS
[18] A SIMPLE ROUTE TO SYN ALPHA-AMINO-BETA-HYDROXY ESTERS BY C-2 REGIOSELECTIVE OPENING OF ALPHA,BETA-EPOXY ESTERS WITH METAL-HALIDES
RIGHI, G
RUMBOLDT, G
BONINI, C
[J]. TETRAHEDRON, 1995, 51 (48) : 13401 - 13408
[19] ROBINSON HG, 1993, COORDINATION CHEM AL
[20] Santelli M., 1995, LEWIS ACIDS SELECTIV

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