Synthesis and resolution of 2-(2-diphenylphosphinyl-naphthalen-1-yl)-l-isopropyl-1H-benzoimidazole;: a new atropisomeric P,N-chelating ligand for asymmetric catalysis

被引：80

作者：

Figge, A

Altenbach, HJ

Brauer, DJ

Tielmann, P

机构：

[1] Berg Univ Gesamthsch Wuppertal, Fachbereich 9, D-42097 Wuppertal, Germany

[2] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(02)00079-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A multistep synthesis resulting in a good yield of the title compound 13 (BIMNAP) has been developed based on N,N-acetal-formation and oxidation with MnO2. The product 11 is converted into the corresponding trifluoromethane sulfonate 12 by treatment with (CF3SO2)(2)O followed by a nickel-catalysed coupling-reaction with HPPh2. Resolution of the phosphanamine 13 was carried out via fractional crystallisation of the diastereomeric hexafluorophosphate salts of the Pd-complex 15, formed from reaction of 13 with (+)-di-mu-chlorobis{2-[1-(dimethylamino)ethyl]phenyl-C,N}dipalladium (S)-14. The absolute configurations of the two diastereomers were determined by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：137 / 144

页数：8

相关论文

共 19 条

[1] SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS [J].

ALCOCK, NW ;

BROWN, JM ;

HULMES, DI .

TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :743-756

[2] CONTRASTING BEHAVIOR OF RELATED PALLADIUM COMPLEX-DERIVED RESOLVING AGENTS - 8-H CONFORMATIONAL LOCKING OF THE 1-NAPHTHYL SIDE-CHAIN [J].

ALCOCK, NW ;

HULMES, DI ;

BROWN, JM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (03) :395-397

[3] SELECTIVE ORTHO LITHIATION OF (2,5-DIMETHOXYPHENYL)DIPHENYLPHOSPHINE OXIDE AND TRAPPING OF THE RESULTING ARYLLITHIUM WITH ELECTROPHILES [J].

BROWN, JM ;

WOODWARD, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6803-6809

[4] SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].

CAI, DW ;

PAYACK, JF ;

BENDER, DR ;

HUGHES, DL ;

VERHOEVEN, TR ;

REIDER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181

[5] Synthesis of 1-methyl-2-diphenylphosphino-3-(1'-isoquinolyl)indole; An easily racemised ligand giving insights into catalytic asymmetric allylation [J].

Claridge, TDW ;

Long, JM ;

Brown, JM ;

Hibbs, D ;

Hursthouse, MB .

TETRAHEDRON, 1997, 53 (11) :4035-4050

[6] GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].

CREMER, D ;

POPLE, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358

[7] Synthesis of 1'-(2-(diarylphosphino)1-naphthyl)isoquinolines; variation of the aryl substituent [J].

Doucet, H ;

Brown, JM .

TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3775-3784

[8] Chiral monodentate phosphine ligand MOP for transition metal-catalyzed asymmetric reactions [J].

Hayashi, T .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :354-362

[9] Enantioselective catalysis with complexes of asymmetric P,N-chelate ligands [J].

Helmchen, G ;

Kudis, S ;

Sennhenn, P ;

Steinhagen, H .

PURE AND APPLIED CHEMISTRY, 1997, 69 (03) :513-518

[10]

Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V1- 3