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.

引用

页码：1593 / 1597

页数：5

共 80 条

[41] Krow G.R., 1993, ORGANIC REACTIONS, V43, P251, DOI DOI 10.1002/0471264180.OR043.03
[42] PODOPHYLLUM-LIGNANE - STRUKTUR UND ABSOLUTKONFIGURATION VON PODORHIZOL-BETA-D-GLUCOSID ([LIGNAN F) .19. MITT UBER MITOSEHEMMENDE NATURSTOFFE
KUHN, M
WARTBURG, A
[J]. HELVETICA CHIMICA ACTA, 1967, 50 (06) : 1546 - &
[43] ASYMMETRIC-SYNTHESIS .6. COPPER SALT PROMOTED GRIGNARD-REAGENT ADDITIONS TO ETHYL 2,3-DIDEOXY-4,5-6,7-DI-O-ISOPROPYLIDENE-D-ARABINO-TRANS-HEPT-2-ENONATEAND SUBSEQUENT FORMATION OF OPTICALLY-ACTIVE 2-ALKYL (OR ARYL) BUTANE-1,4-DIOIC ACIDS AND BUTYRO-1,4-LACTONES
LAWSTON, IW
INCH, TD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (11): : 2629 - 2635
[44] Asymmetric Baeyer-Villiger oxidation of cyclobutanones
Lopp, M
Paju, A
Kanger, T
Pehk, T
[J]. TETRAHEDRON LETTERS, 1996, 37 (42) : 7583 - 7586
[45] ASYMMETRIC HETERO-DIELS-ALDER REACTION CATALYZED BY CHIRAL ORGANO-ALUMINUM REAGENT
MARUOKA, K
ITOH, T
SHIRASAKA, T
YAMAMOTO, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (01) : 310 - 312
[46] MARUOKA K, 1993, CATALYTIC ASYMMETRIC, P413
[47] A chemoenzymatic strategy for the synthesis of enantiopure (R)-(-)-baclofen
Mazzini, C
Lebreton, J
Alphand, V
Furstoss, R
[J]. TETRAHEDRON LETTERS, 1997, 38 (07) : 1195 - 1196
[48] Ooi T., 1999, COMPREHENSIVE ASYMME, V3, P1237
[49] New chiral complexes of platinum(II) as catalysts for the enantioselective Baeyer-Villiger oxidation of ketones with hydrogen peroxide:: Dissymmetrization of meso-cyclohexanones
Paneghetti, C
Gavagnin, R
Pinna, F
Strukul, G
[J]. ORGANOMETALLICS, 1999, 18 (24) : 5057 - 5065
[50] ASYMMETRIC-SYNTHESIS OF DIBENZYLBUTYROLACTONES AND ARYLTETRALIN LIGNAN LACTONES BY TANDEM CONJUGATE ADDITION TO A CHIRAL BUTENOLIDE
PELTER, A
WARD, RS
JONES, DM
MADDOCKS, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (21): : 2621 - 2629

← 1 2 3 4 5 6 7 8 →