Chiral aluminum complexes as catalysts in asymmetric Baeyer-Villiger reactions of cyclobutanones

被引：51
作者：
Bolm, C [1 ]
Beckmann, O [1 ]
Palazzi, C [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
来源：
CANADIAN JOURNAL OF CHEMISTRY | 2001年 / 79卷 / 11期
关键词：
aluminum; asymmetric catalysis; lactones; oxidations; rearrangement;
D O I：
10.1139/cjc-79-11-1593
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
BINOL-aluminum complexes were successfully employed as mediators and catalysts in asymmetric Baeyer-Villiger rearrangements of cyclobutanones. Good enantioselectivies were achieved with only 15 mol% of the chosen chiral Lewis acid. The enantiomeric excesses obtained have never been reached before in such metal-catalyzed Baeyer-Villiger reactions.
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页码：1593 / 1597
页数：5
相关论文
共 80 条
[1]   Catalytic enantioselective ring-closing metathesis by a chiral biphen-Mo complex [J].
Alexander, JB ;
La, DS ;
Cefalo, DR ;
Hoveyda, AH ;
Schrock, RR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4041-4042
[2]   MICROBIAL TRANSFORMATIONS .16. ONE-STEP SYNTHESIS OF A PIVOTAL PROSTAGLANDIN CHIRAL SYNTHON VIA A HIGHLY ENANTIOSELECTIVE MICROBIOLOGICAL BAEYER-VILLIGER TYPE REACTION [J].
ALPHAND, V ;
ARCHELAS, A ;
FURSTOSS, R .
TETRAHEDRON LETTERS, 1989, 30 (28) :3663-3664
[3]  
Baeyer A., 1899, Ber. Dtsch. Chem. Ges., V32, P3625, DOI 10.1002/cber.189903203151
[4]   VAULTED BIARYLS AS CHIRAL LIGANDS FOR ASYMMETRIC CATALYTIC DIELS-ALDER REACTIONS [J].
BAO, JM ;
WULFF, WD ;
RHEINGOLD, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) :3814-3815
[5]  
Bergner EJ, 2000, EUR J ORG CHEM, V2000, P419, DOI 10.1002/(SICI)1099-0690(200002)2000:3<419::AID-EJOC419>3.0.CO
[6]  
2-N
[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]  
Bolm C, 1997, ADV CAT PROCESS, V2, P43
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