Copper- and vanadium-catalyzed asymmetric oxidations

被引:115
作者
Bolm, C [1 ]
Schlingloff, G [1 ]
Bienewald, F [1 ]
机构
[1] UNIV MARBURG, FACHBEREICH CHEM, D-35032 MARBURG, GERMANY
关键词
Baeyer-Villiger oxidation; asymmetric catalysis; sulfide oxidation;
D O I
10.1016/S1381-1169(96)00359-7
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Two asymmetric metal-catalyzed oxidations are discussed. Chiral copper complexes catalyze enantiospecific Baeyer-Villiger oxidations giving optically active lactones in up to 95% ee. Vanadium complexes have been used in enantioselective sulfide oxidations with hydrogen peroxide.
引用
收藏
页码:347 / 350
页数:4
相关论文
共 32 条
[1]   ENZYMATIC BAEYER-VILLIGER TYPE OXIDATIONS OF KETONES CATALYZED BY CYCLOHEXANONE OXYGENASE [J].
ABRIL, O ;
RYERSON, CC ;
WALSH, C ;
WHITESIDES, GM .
BIOORGANIC CHEMISTRY, 1989, 17 (01) :41-52
[2]   MICROBIOLOGICAL TRANSFORMATIONS .22. MICROBIOLOGICALLY MEDIATED BAEYER-VILLIGER REACTIONS - A UNIQUE ROUTE TO SEVERAL BICYCLIC GAMMA-LACTONES IN HIGH ENANTIOMERIC PURITY [J].
ALPHAND, V ;
FURSTOSS, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1306-1309
[3]  
AZERAD R, 1995, B SOC CHIM FR, V132, P17
[4]  
Baeyer A., 1899, BER DTSCH CHEM GES, V32, P3625, DOI [10.1002/cber.189903203151, DOI 10.1002/CBER.189903203151]
[5]  
Berrisford D.J., 1995, ANGEW CHEM, V107, P1159
[6]   LIGAND-ACCELERATED CATALYSIS [J].
BERRISFORD, DJ ;
BOLM, C ;
SHARPLESS, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (10) :1059-1070
[7]  
Bolm C, 1995, ANGEW CHEM INT EDIT, V34, P2640
[8]   USE OF MOLECULAR-OXYGEN IN THE BAEYER-VILLIGER OXIDATION THE INFLUENCE OF METAL-CATALYSTS [J].
BOLM, C ;
SCHLINGLOFF, G ;
WEICKHARDT, K .
TETRAHEDRON LETTERS, 1993, 34 (21) :3405-3408
[9]   METAL-CATALYZED ENANTIOSPECIFIC AEROBIC OXIDATION OF CYCLOBUTANONES [J].
BOLM, C ;
SCHLINGLOFF, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (12) :1247-1248
[10]   OPTICALLY-ACTIVE LACTONES FROM A BAEYER-VILLIGER-TYPE METAL-CATALYZED OXIDATION WITH MOLECULAR-OXYGEN [J].
BOLM, C ;
SCHLINGLOFF, G ;
WEICKHARDT, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (18) :1848-1849