Enantioselective reduction of prochiral ketones by catecholborane catalysed by chiral group 13 complexes

被引：0

作者：

Blake, AJ

Cunningham, A

Ford, A

Teat, SJ

Woodward, S

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] SERC, Daresbury Lab, Warrington WA4 4AD, Cheshire, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2000年 / 6卷 / 19期

关键词：

asymmetric catalysis; gallium; indium; S ligands;

D O I：

10.1002/1521-3765(20001002)6:19<3586::AID-CHEM3586>3.0.CO;2-S

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

LiGaH4, in combination with the S,O-chelate 2-hydroxy-2'-mercapto-1,1'-binaphthyl (MTBH2), forms an active catalyst for the asymmetric reduction of prochiral ketones, with catecholborane as the hydride source. Enantioface differentiation is on the basis of the steric requirements of the ketone substituents. Aryl/n-alkyl ketones are reduced in 90-93% ee and RC(O)Me (e.g. R = iPr, cycloC(6)H(11), tBu) in 60-72% ee. Other borane sources and alternative catalyst structures based on indium do not form enantioselective catalysts.

引用

收藏

页码：3586 / 3594

页数：9

相关论文

共 44 条

[1] COMPLETION AND REFINEMENT OF CRYSTAL-STRUCTURES WITH SIR92 [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, C ;

GUAGLIARDI, A .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1993, 26 (pt 3) :343-350

[2]

[Anonymous], 1996, SADABS PROGRAM SCALI

[3] LITHIUM BOROHYDRIDE-CATALYZED SELECTIVE REDUCTION OF CARBONYL GROUP OF CONJUGATED AND UNCONJUGATED ALKENONES WITH BORANE IN TETRAHYDROFURAN [J].

ARASE, A ;

HOSHI, M ;

YAMAKI, T ;

NAKANISHI, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (07) :855-856

[4] Catalytic conjugate addition promoted by the copper(I)-monothiobinaphthol system .2. Optimal ligand synthesis and initial catalytic results [J].

Azad, SM ;

Bennett, SMW ;

Brown, SM ;

Green, J ;

Sinn, E ;

Topping, CM ;

Woodward, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (05) :687-694

[5] Mathematical models of nonlinear effects in asymmetric catalysis: New insights based on the role of reaction rate [J].

Blackmond, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (52) :12934-12939

[6]

*BRUK AXS, 1997, SMART SAINT AR DET C

[7] THE CHEMOSELECTIVE CYCLIZATION OF UNSYMMETRICAL GAMMA-DIKETONES TO CYCLOPENTENONES BY DIRECTED ALDOL REACTION USING A MAGNESIUM CHELATE [J].

CADMAN, MLF ;

CROMBIE, L ;

FREEMAN, S ;

MISTRY, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (11) :1397-1407

[8] SIMPLE AND EFFICIENT RESOLUTION OF 1,1'-BI-2-NAPHTHOL [J].

CAI, DW ;

HUGHES, DL ;

VERHOEVEN, TR ;

REIDER, PJ .

TETRAHEDRON LETTERS, 1995, 36 (44) :7991-7994

[9] A new high-flux chemical and materials crystallography station at the SRS Daresbury .1. Design, construction and test results [J].

Cernik, RJ ;

Clegg, W ;

Catlow, CRA ;

BushnellWye, G ;

Flaherty, JV ;

Greaves, GN ;

Burrows, I ;

Taylor, DJ ;

Teat, SJ ;

Hamichi, M .

JOURNAL OF SYNCHROTRON RADIATION, 1997, 4 :279-286

[10] A novel titanium-oxygen ladder structure supported by calix[4]arene ligands, characterised by synchrotron crystallography [J].

Clegg, W ;

Elsegood, MRJ ;

Teat, SJ ;

Redshaw, C ;

Gibson, VC .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (18) :3037-3039

← 1 2 3 4 5 →