New route to biaryl phosphanes with axial chirality as ligands for enantioselective hydrogenations

被引：18

作者：

Driessen-Hölscher, BD

Kralik, J

Agel, F

Steffens, C

Hu, CH

机构：

[1] Rhein Westfal TH Aachen, Inst Tech Chem & Macromol Chem, D-33098 Paderborn, Germany

[2] Univ Gesamthsch Paderborn, Fac Sci, D-33098 Paderborn, Germany

[3] Rhein Westfal TH Aachen, Inst Inorgan Chem, D-52056 Aachen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 08期

关键词：

asymmetric hydrogenation; atropisomeric diaryl-core diphosphanes; crystal structure determination; dimethyl itaconate; homogeneous catalysis; P ligands; ruthenium;

D O I：

10.1002/adsc.200404034

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We have found a modular route for the synthesis of Cl-MeO BIPHEP ligands via the corresponding biphenol that allows us to introduce several substituents without the necessity to separate the enantiomers of each derivative. These new diphosphanes were used in the ruthenium-catalyzed enantioselective hydrogenation of dimethyl itaconate with ee values up to 97%.

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收藏

页码：979 / 982

页数：4

相关论文

共 14 条

[1] Selective hydrogenation for fine chemicals: Recent trends and new developments [J].

Blaser, HU ;

Malan, C ;

Pugin, B ;

Spindler, F ;

Steiner, H ;

Studer, M .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151

[2]

Brown J. M, 1999, COMPREHENSIVE ASYMME, VI, P121

[3]

Daley CJA, 1998, CAN J CHEM, V76, P1447

[4] NEW EFFICIENT METHODS FOR THE SYNTHESIS AND INSITU PREPARATION OF RUTHENIUM(II) COMPLEXES OF ATROPISOMERIC DIPHOSPHINES AND THEIR APPLICATION IN ASYMMETRIC CATALYTIC HYDROGENATIONS [J].

HEISER, B ;

BROGER, EA ;

CRAMERI, Y .

TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :51-62

[5] Water soluble phosphines .8. Palladium-catalyzed P-C cross coupling reactions between primary or secondary phosphines and functional aryliodides - A novel synthetic route to water soluble phosphines [J].

Herd, O ;

Hessler, A ;

Hingst, M ;

Tepper, M ;

Stelzer, O .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 522 (01) :69-76

[6] Difluorphos, an electron-poor diphosphane: A good match between electronic and steric features [J].

Jeulin, S ;

de Paule, SB ;

Ratovelomanana-Vidal, V ;

Genet, JP ;

Champion, N ;

Dellis, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (03) :320-325

[7]

KRALIK J, 2000, Patent No. 10044793

[8] Palladium-catalyzed phosphination of functionalized aryl triflates [J].

Kwong, FY ;

Lai, CW ;

Yu, M ;

Tian, Y ;

Chan, KS .

TETRAHEDRON, 2003, 59 (51) :10295-10305

[9] Synthesis of biaryl P,N ligands by novel palladium-catalyzed phosphination using triarylphosphines:: Catalytic application of C-P activation [J].

Kwong, FY ;

Chan, KS .

ORGANOMETALLICS, 2000, 19 (11) :2058-2060

[10]

LAUE C, 1996, Patent No. 749973