Phosphinamides catalysts containing a stereogenic phosphorus atom for the asymmetric reduction of ketones by borane

被引：36

作者：

Burns, B

Gamble, MP

Simm, ARC

Studley, JR

Alcock, NW

Wills, M

机构：

[1] UNIV WARWICK,DEPT CHEM,COVENTRY CV4 7AL,W MIDLANDS,ENGLAND

[2] UNIV BATH,SCH CHEM,BATH BA7 2AY,AVON,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 01期

关键词：

D O I：

10.1016/S0957-4166(96)00482-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The effect of the configuration of the phosphorus atom in phosphinamide reduction catalysts has been studied through the preparation and use of a series of catalysts containing stereogenic phosphorus atoms of known configuration. The conclusion of this work is that a stereogenic centre at phosphorus can improve the selectivity of reductions using this catalyst, but is not sufficient in itself to generate the higher levels of selectivity which have been achieved with related catalysts. The X-ray crystallographic structure of a key compound is also featured. (C) 1997, Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：73 / 78

页数：6

相关论文

共 11 条

[1] ENANTIOSELECTIVE REDUCTION OF KETONES WITH BORANE, CATALYZED BY (S)-(-)-PROLINE OR (S)-(+)-PROLINOL [J].

BRUNEL, JM ;

MAFFEI, M ;

BUONO, G .

TETRAHEDRON-ASYMMETRY, 1993, 4 (10) :2255-2260

[2] NEW CATALYSTS CONTAINING AN N-P=O STRUCTURAL UNIT FOR THE ASYMMETRIC REDUCTION OF KETONES [J].

BURNS, B ;

STUDLEY, JR ;

WILLS, M .

TETRAHEDRON LETTERS, 1993, 34 (44) :7105-7106

[3] STEREOELECTRONIC REQUIREMENTS FOR A NEW CLASS OF ASYMMETRIC KETONE REDUCTION CATALYSTS CONTAINING AN N-P=O STRUCTURAL UNIT [J].

BURNS, B ;

KING, NP ;

STUDLEY, JR ;

TYE, H ;

WILLS, M .

TETRAHEDRON-ASYMMETRY, 1994, 5 (05) :801-804

[4] Enantioselective reduction of ketones by borane catalysed by oxazaphospholidine oxides [J].

Chiodi, O ;

Fotiadu, F ;

Sylvestre, M ;

Buono, G .

TETRAHEDRON LETTERS, 1996, 37 (01) :39-42

[5] A NITROGEN-GAS-STREAM CRYOSTAT FOR GENERAL X-RAY-DIFFRACTION STUDIES [J].

COSIER, J ;

GLAZER, AM .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1986, 19 (02) :105-107

[6] The oxazaborolidine-borane reduction of ketones: Identification and reactivity of transient intermediates [J].

Douglas, AW ;

Tschaen, DM ;

Reamer, RA ;

Shi, YJ .

TETRAHEDRON-ASYMMETRY, 1996, 7 (05) :1303-1308

[7] New chiral phosphinamide catalysts for highly enantioselective reduction of ketones. [J].

Gamble, MP ;

Studley, JR ;

Wills, M .

TETRAHEDRON LETTERS, 1996, 37 (16) :2853-2856

[8]

GAMBLE MP, 1996, UNPUB TETRAHEDRON AS, V7, P3071

[9] THE SYNTHESIS OF OPTICALLY-ACTIVE P-PHENYL-P-(2,4,6-TRIMETHYLPHENYL)PHOSPHINAMIDE AND AN X-RAY STRUCTURE OF (-)-(1R)-N-(1-PHENYLETHYL)(SP)-P-PHENYL-P-(2,4,6-TRIMETHYLPHENYL)PHOSPHINAMIDE [J].

HAMOR, TA ;

JENNINGS, WB ;

LOVELY, CJ ;

REEVES, KA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (05) :843-849

[10]

SHELDRICK GM, 1996, SHELX 96 BETA TEST