Asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones using a chiral cationic Palladium(II) 2-(phosphinophenyl)pyridine complex as catalyst

被引:36
作者
Ito, K [1 ]
Ishii, A
Kuroda, T
Katsuki, T
机构
[1] Fukuoka Univ Educ, Dept Chem, CREST, JST, Fukuoka 8114192, Japan
[2] Kyushu Univ 33, Dept Chem, Fac Sci, Grad Sch,CREST,JST,Higashi Ku, Fukuoka 8128581, Japan
关键词
asymmetric Baeyer-Villiger oxidation; asymmetric catalysis; palladium; chiral P-N ligand;
D O I
10.1055/s-2003-38377
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral cationic palladium(II) 2-(phosphinophenyl)pyridine (1a) complex was found to be an effective catalyst for asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones. For example, good and excellent enantioselectivities (80% and >99% ees) were achieved in the reactions of 3-phenylcyclobutanone and a tricyclic cyclobutanone, respectively.
引用
收藏
页码:643 / 646
页数:4
相关论文
共 46 条
[1]  
ALPHAND V, 2001, ASYMMETRIC OXIDATION, P214
[2]  
ALPHAND V, 1995, HDB ENZYME CATALYSIS, V2, P744
[3]  
Aoki M, 2001, HELV CHIM ACTA, V84, P187, DOI 10.1002/1522-2675(20010131)84:1<187::AID-HLCA187>3.0.CO
[4]  
2-O
[5]   Chiral aluminum complexes as catalysts in asymmetric Baeyer-Villiger reactions of cyclobutanones [J].
Bolm, C ;
Beckmann, O ;
Palazzi, C .
CANADIAN JOURNAL OF CHEMISTRY, 2001, 79 (11) :1593-1597
[6]  
Bolm C, 2001, SYNLETT, P1461
[7]   Copper- and vanadium-catalyzed asymmetric oxidations [J].
Bolm, C ;
Schlingloff, G ;
Bienewald, F .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 117 (1-3) :347-350
[8]   METAL-CATALYZED ENANTIOSPECIFIC AEROBIC OXIDATION OF CYCLOBUTANONES [J].
BOLM, C ;
SCHLINGLOFF, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (12) :1247-1248
[9]  
Bolm C, 1997, SYNLETT, P1151
[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