Recent developments in the application of oxazoline-containing ligands in asymmetric catalysis

被引：649

作者：

McManus, HA ^{[1
]}

Guiry, PJ ^{[1
]}

机构：

[1] Univ Coll Dublin, Dept Chem, Conway Inst Biomol & Biomed Res, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

CHEMICAL REVIEWS | 2004年 / 104卷 / 09期

关键词：

D O I：

10.1021/cr040642v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This review covers recent developments in the design of oxazaline-based ligands for asymmetric catalysis. In particular, new mono(oxazoline), bis(oxazoline) and tris(oxazoline) ligands, which were reported in the literature between 1998 and 2003, are discussed. The range of utility of this class of ligands in catalytic asymmetric synthesis is demonstrated by the high enantiocontrol induced in a diverse array of metal-catalyzed transformations ranging from oxidations and reductions to cycloadditions and carbon-carbon bond-forming reactions.

引用

页码：4151 / 4202

页数：52

共 243 条

[1] Pd-Catalyzed asymmetric allylic alkylations using various diphenylphosphino(oxazolinyl)ferrocene ligands [J].

Ahn, KH ;

Cho, CW ;

Park, JW ;

Lee, SW .

TETRAHEDRON-ASYMMETRY, 1997, 8 (08) :1179-1185

[2] cis-Selective cyclopropanations using chiral 5,5-diaryl bis(oxazoline) catalysts [J].

Alexander, K ;

Cook, S ;

Gibson, CL .

TETRAHEDRON LETTERS, 2000, 41 (36) :7135-7138

[3] PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS [J].

ALLEN, JV ;

COOTE, SJ ;

DAWSON, GJ ;

FROST, CG ;

MARTIN, CJ ;

WILLIAMS, JMJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15) :2065-2072

[4] ENANTIOMERICALLY PURE OXAZOLINES TETHERED TO ALCOHOLS - PREPARATION AND USE IN ASYMMETRIC CATALYSIS [J].

ALLEN, JV ;

WILLIAMS, JMJ .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :277-282

[5] ASYMMETRIC ADDITION OF DIETHYLZINC TO AROMATIC-ALDEHYDES USING ENANTIOMERICALLY PURE HYDROXYMETHYL OXAZOLINE LIGANDS [J].

ALLEN, JV ;

FROST, CG ;

WILLIAMS, JMJ .

TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :649-650

[6] Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones: Mechanism and origin of enantioselectivity [J].

Alonso, DA ;

Brandt, P ;

Nordin, SJM ;

Andersson, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9580-9588

[7] Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity [J].

Anderson, CE ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12412-12413

[8] Synthesis and preliminary use of naphthyl quinazoline and isoquinoline oxazolines for asymmetric allylic oxidation [J].

Andrus, MB ;

Sekhar, BBVS .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (06) :1265-1271

[9] Efficient synthesis of 1,1′-binaphthyl and 2,2′-bi-o-tolyl-2,2′-bis(oxazoline)s and preliminary use for the catalytic asymmetric allylic oxidation of cyclohexene [J].

Andrus, MB ;

Asgari, D ;

Sclafani, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9365-9368

[10]

Annunziata R, 2003, EUR J ORG CHEM, V2003, P1191

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