Synthesis of chiral 2,2′-dipyridylamines and their use in the copper-catalyzed asymmetric allylic oxidation of cyclohexene

被引：18

作者：

Bolm, C ^{[1
]}

Frison, JC ^{[1
]}

Le Paih, J ^{[1
]}

Moessner, C ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 26期

关键词：

allylic oxidation; N-arylation; copper catalysis; 2,2 '-dipyridylamines;

D O I：

10.1016/j.tetlet.2004.05.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral dipyridylamines have been synthesized by N-arylation reactions, and the applicability of those compounds to the copper-catalyzed asymmetric allylic oxidation of cyclohexene was demonstrated. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5019 / 5021

页数：3

共 27 条

[1] Copper catalyzed allylic oxidation with peresters
Andrus, MB
Lashley, JC
[J]. TETRAHEDRON, 2002, 58 (05) : 845 - 866
[2] ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE PYRIDINE-DERIVATIVES AND C-2-SYMMETRICAL 2,2'-BIPYRIDINES
BOLM, C
EWALD, M
FELDER, M
SCHLINGLOFF, G
[J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05): : 1169 - 1190
[3] Palladium-catalyzed N-arylation of sulfoximines with aryl bromides and aryl iodides
Bolm, C
Hildebrand, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) : 169 - 175
[4] BOLM C, 1991, ADV ORGANIC SYNTHESI, P223
[5] Chiral 2,2′-bipyridines, 1,10-phenanthrolines, and 2,2′:6′,2"-terpyridines:: Syntheses and applications in asymmetric homogeneous catalysis
Chelucci, G
Thummel, RP
[J]. CHEMICAL REVIEWS, 2002, 102 (09) : 3129 - 3170
[6] Design of a new class of chiral C2-symmetric dipyridylmethane ligands and their application in asymmetric catalysis
Chelucci, G
Loriga, G
Murineddu, G
Pinna, GA
[J]. TETRAHEDRON LETTERS, 2002, 43 (47) : 8599 - 8602
[7] Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis
Fache, F
Schulz, E
Tommasino, ML
Lemaire, M
[J]. CHEMICAL REVIEWS, 2000, 100 (06) : 2159 - 2231
[8] Chiral 2,2′-bipyridines:: ligands for asymmetric induction
Fletcher, NC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (16): : 1831 - 1842
[9] THE CHEMISTRY OF 2-OXAZOLINES (1985-PRESENT)
GANT, TG
MEYERS, AI
[J]. TETRAHEDRON, 1994, 50 (08) : 2297 - 2360
[10] Harmata M., 2003, CHEMTRACTS, V16, P660

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