Efficient and selective catalytic oxidative cleavage of α-hydroxy ketones using vanadium-based HPA and dioxygen

被引：48

作者：

El Aakel, L

Launay, F

Atlamsani, A

Brégeault, JM

机构：

[1] Univ Paris 06, CNRS, Lab Syst Interfaciaux Echelle Nanometr, Unite 2312, F-75252 Paris 05, France

[2] Univ Abdelmalek Essaadi, Fac Sci, Dept Chim, Lab Chim Phys Appl, Tetouan 93000, Morocco

来源：

CHEMICAL COMMUNICATIONS | 2001年 / 21期

关键词：

D O I：

10.1039/b106969a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The combination of H3+n[PMo12-nVnO40]. aq (HPA- n, n = 3) and dioxygen provides a clean and regioselective reagent for the homolytic cleavage of various representative a hydroxy ketones (primary to tertiary) and turns out to be as efficient for the catalytic ring opening of chiral natural products.

引用

收藏

页码：2218 / 2219

页数：2

相关论文

共 22 条

[11] THE OXIDATION OF KETONES WITH A HETEROPOLYACID, H5[PMO10V2O40] AND DIOXYGEN [J].

ELALI, B ;

BREGEAULT, JM ;

MERCIER, J ;

MARTIN, J ;

MARTIN, C ;

CONVERT, O .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (13) :825-826

[12] CLEAVAGE OF UNSATURATED ALPHA-KETOLS TO OMEGA-OXO-ALPHA,BETA-UNSATURATED ACIDS [J].

FLORESCA, R ;

KURIHARA, M ;

WATT, DS ;

DEMIR, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2196-2200

[13] AN ENANTIOSELECTIVE APPROACH TO RING A OF TAXOL USING THE WIELAND-MIESCHER KETONE [J].

GOLINSKI, M ;

VASUDEVAN, S ;

FLORESCA, R ;

BROCK, CP ;

WATT, DS .

TETRAHEDRON LETTERS, 1993, 34 (01) :55-58

[14]

KARPF M, 1981, J AM CHEM SOC, V103, P302, DOI 10.1021/ja00392a009

[15] Highly chemoselective, oxyvanadium-catalysed cleavage of α-hydroxy ketones [J].

Kirihara, M ;

Takizawa, S ;

Momose, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (01) :7-8

[16] Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid-phase reactions [J].

Kozhevnikov, IV .

CHEMICAL REVIEWS, 1998, 98 (01) :171-198

[17] Divergent routes to chiral cyclobutane synthons from (-)-α-pinene and their use in the stereoselective synthesis of dehydro amino acids [J].

Moglioni, AG ;

García-Expósito, E ;

Aguado, GP ;

Parella, T ;

Branchadell, V ;

Moltrasio, GY ;

Ortuño, RM .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13) :3934-3940

[18] MODEL STUDIES OF TERPENE BIOSYNTHESIS - SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (+)-TRANS-2,2-DIMETHYL-3-(2'-METHYLPROPENYL)CYCLOBUTANOL [J].

MUSCIO, OJ ;

POULTER, CD .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (22) :3288-3291

[19] OXIDATIVE CLEAVAGE OF ALPHA-DIOLS, ALPHA-DIONES, ALPHA-HYDROXY-KETONES AND ALPHA-HYDROXY ACIDS AND ALPHA-KETO ACIDS WITH CALCIUM HYPOCHLORITE [CA(OC1)2] [J].

NWAUKWA, SO ;

KEEHN, PM .

TETRAHEDRON LETTERS, 1982, 23 (31) :3135-3138

[20] AMBERLYST-15 - A PRACTICAL, MILD AND SELECTIVE CATALYST FOR METHYL ESTERIFICATION OF CARBOXYLIC-ACIDS [J].

PETRINI, M ;

BALLINI, R ;

MARCANTONI, E ;

ROSINI, G .

SYNTHETIC COMMUNICATIONS, 1988, 18 (08) :847-853