Vaulted biaryls: Efficient ligands for the aluminum-catalyzed asymmetric Baeyer-Villiger reaction

被引：42

作者：

Bolm, C

Frison, JC

Zhang, Y

Wulff, WD

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

[2] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

来源：

SYNLETT | 2004年 / 09期

关键词：

aluminium; asymmetric catalysis; Baeyer-Villiger reaction; biaryls; lactones;

D O I：

10.1055/s-2004-829080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vaulted biaryls (VANOL and VAPOL) have been applied in the aluminum-catalyzed asymmetric Baeyer-Villiger reaction of prochiral 3-substituted cyclobutanones. Optically active gamma-butyrolactones are obtained in high yields with enantioselectivities of up to 84% ee.

引用

页码：1619 / 1621

页数：3

共 26 条

[1] Catalytic asymmetric aziridination with a chiral VAPOL-boron Lewis acid
Antilla, JC
Wulff, WD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) : 5099 - 5100
[2] Antilla JC, 2000, ANGEW CHEM INT EDIT, V39, P4518
[3] VAULTED BIARYLS AS CHIRAL LIGANDS FOR ASYMMETRIC CATALYTIC DIELS-ALDER REACTIONS
BAO, JM
WULFF, WD
RHEINGOLD, AL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) : 3814 - 3815
[4] Chiral aluminum complexes as catalysts in asymmetric Baeyer-Villiger reactions of cyclobutanones
Bolm, C
Beckmann, O
Palazzi, C
[J]. CANADIAN JOURNAL OF CHEMISTRY, 2001, 79 (11) : 1593 - 1597
[5] Bolm C, 1997, ADV CAT PROCESS, V2, P43
[6] Bolm C, 1999, MED RES REV, V19, P348, DOI 10.1002/(SICI)1098-1128(199909)19:5<348::AID-MED3>3.0.CO
[7] 2-U
[8] Influence of hydroperoxides on the enantioselectivity of metal-catalyzed asymmetric Baeyer-Villiger oxidation and epoxidation with chiral ligands
Bolm, C
Beckmann, O
Kühn, T
Palazzi, C
Adam, W
Rao, PB
Saha-Möller, CR
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (17) : 2441 - 2446
[9] Bolm C., 1999, COMPREHENSIVE ASYMME, V2, P803
[10] BOLM C, 1998, TRANSITION METALS OR, V2, P213

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