Enantioselective allylic substitution using a novel (phosphino-α-D-glucopyrano-oxazoline)palladium catalyst

被引：70

作者：

Glaser, B ^{[1
]}

Kunz, H ^{[1
]}

机构：

[1] Univ Mainz, Inst Organ Chem, D-55099 Mainz, Germany

来源：

SYNLETT | 1998年 / 01期

关键词：

enantioselective catalysis; palladium-catalyzed allylation; P; N-ligand; carbohydrate-derived ligand; glucosamine;

D O I：

10.1055/s-1998-3124

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel enantiomerically pure 2-[2(diphenylphosphino)phenyl] -4,5-(2-deoxy-alpha-D-glucopyrano)-oxazoline ligand (6) was prepared from glucosamine (1). The stereodifferentiating potential of the ligand 6 was demonstrated in palladium-catalyzed intermolecular allylic substitutions of symmetrically and non symmetrically substituted allyl acetates which give products in high yields and high enantioselectivity (up to 98 % ee).

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页码：53 / +

页数：3

相关论文

共 28 条

[1] PREPARATION OF NOVEL SULFUR AND PHOSPHORUS-CONTAINING OXAZOLINES AS LIGANDS FOR ASYMMETRIC CATALYSIS [J].

ALLEN, JV ;

DAWSON, GJ ;

FROST, CG ;

WILLIAMS, JMJ ;

COOTE, SJ .

TETRAHEDRON, 1994, 50 (03) :799-808

[2] LIGAND ELECTRONIC EFFECTS IN ASYMMETRIC CATALYSIS - ENHANCED ENANTIOSELECTIVITY IN THE ASYMMETRIC HYDROCYANATION OF VINYLARENES [J].

CASALNUOVO, AL ;

RAJANBABU, TV ;

AYERS, TA ;

WARREN, TH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :9869-9882

[3] ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS [J].

DAWSON, GJ ;

FROST, CG ;

WILLIAMS, JMJ .

TETRAHEDRON LETTERS, 1993, 34 (19) :3149-3150

[4] ENANTIOSELECTIVE SYNTHESIS OF SUCCINIC ACIDS AND GAMMA-LACTONES VIA PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS [J].

DAWSON, GJ ;

WILLIAMS, JMJ ;

COOTE, SJ .

TETRAHEDRON-ASYMMETRY, 1995, 6 (10) :2535-2546

[5] SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION [J].

FROST, CG ;

HOWARTH, J ;

WILLIAMS, JMJ .

TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1089-1122

[6] UBERFUHRUNG VON D-GLUCOSAMIN IN OXAZOLONDERIVATE UND OXAZOLINDERIVATE [J].

KONSTAS, S ;

PHOTAKI, I ;

ZERVAS, L .

CHEMISCHE BERICHTE-RECUEIL, 1959, 92 (06) :1288-1293

[7] CARBOHYDRATE PHOSPHINITES AS CHIRAL LIGANDS FOR ASYMMETRIC SYNTHESES CATALYZED BY COMPLEXES .11. INCREASE IN THE ENANTIOSELECTIVITY OF ASYMMETRIC HYDROGENATION IN WATER INFLUENCED BY SURFACTANTS OR POLYMERIZED MICELLES [J].

KUMAR, A ;

OEHME, G ;

ROQUE, JP ;

SCHWARZE, M ;

SELKE, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (21) :2197-2199

[8]

KUMAR A, 1994, ANGEW CHEM, V106, P2272

[9] STEREOSELECTIVE SYNTHESES USING CARBOHYDRATES AS CHIRAL AUXILIARIES [J].

KUNZ, H .

PURE AND APPLIED CHEMISTRY, 1995, 67 (10) :1627-1635

[10] CARBOHYDRATES AS CHIRAL AUXILIARIES IN STEREOSELECTIVE SYNTHESIS [J].

KUNZ, H ;

RUCK, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (03) :336-358