Practical preparation and resolution of 1-(2′-diphenylphosphino-1′-naphthyl)isoquinoline:: A useful ligand for catalytic asymmetric synthesis

被引：134

作者：

Lim, CW

Tissot, O

Mattison, A

Hooper, MW

Brown, JM ^{[1
]}

Cowley, AR

Hulmes, DI

Blacker, AJ

机构：

[1] Dyson Perrins Lab, S Parks Rd, Oxford OX1 3QY, England

[2] Chem Crystallog Lab, Oxford OX1, England

[3] Avecia PLC, Huddersfield, W Yorkshire, England

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2003年 / 7卷 / 03期

关键词：

D O I：

10.1021/op034007n

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A practical synthesis of the atropisomerically chiral ligand QUINAP is described, followed by its efficient resolution into enantiomers by employing a deficiency of the chloropalladium complex derived from 1'-(R)-1'-(dimethylamino)-1-ethylnaphthalene. The X-ray structure of the ligand, which crystallises as a conglomerate, is reported.

引用

收藏

页码：379 / 384

页数：6

相关论文

共 50 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]

ALCOCK NW, 1995, CHEM COMMUN, P395

[3] RESOLUTIONS INVOLVING METAL COMPLEXATION - PREPARATION AND RESOLUTION OF (R,S)-METHYLPHENYL(8-QUINOLYL)PHOSPHINE AND ITS ARSENIC ANALOG - CRYSTAL AND MOLECULAR-STRUCTURE OF (+)589-[(R)-DIMETHYL(1-ETHYL-ALPHA-NAPHTHYL)AMINATO-C-2, N][(S)-METHYLPHENYL(8-QUINOLYL)PHOSPHINE]PALLADIUM(II) HEXAFLUOROPHOSPHATEOG [J].

ALLEN, DG ;

MCLAUGHLIN, GM ;

ROBERTSON, GB ;

STEFFEN, WL ;

SALEM, G ;

WILD, SB .

INORGANIC CHEMISTRY, 1982, 21 (03) :1007-1014

[4] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[5]

[Anonymous], 1972, Inorg. Synth, DOI DOI 10.1002/9780470132449.CH23

[6] Stereoselectivity in the mass-spectral fragmentation of palladium phosphinamine complexes [J].

Aplin, RT ;

Doucet, H ;

Hooper, MW ;

Brown, JM .

CHEMICAL COMMUNICATIONS, 1997, (21) :2097-2098

[7] MECHANICAL ACTIVATION OF MAGNESIUM TURNINGS FOR THE PREPARATION OF REACTIVE GRIGNARD-REAGENTS [J].

BAKER, KV ;

BROWN, JM ;

HUGHES, N ;

SKARNULIS, AJ ;

SEXTON, A .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :698-703

[8] MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].

BROWN, JM ;

HULMES, DI ;

GUIRY, PJ .

TETRAHEDRON, 1994, 50 (15) :4493-4506

[9]

BROWN JM, 1995, Patent No. 9513284

[10]

BROWN JM, 1993, CHEM COMMUN, P1673

← 1 2 3 4 5 →