A polymer-enlarged homogeneously soluble oxazaborolidine catalyst for the asymmetric reduction of ketones by borane

被引：64

作者：

Felder, M ^{[1
]}

Giffels, G ^{[1
]}

Wandrey, C ^{[1
]}

机构：

[1] FORSCHUNGSZENTRUM JULICH, FORSCHUNGSZENTRUM, INST BIOTECHNOL, D-52425 JULICH, GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(97)00192-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A polymer-enlarged homogeneously soluble oxazaborolidine catalyst has been prepared and used in the enantioselective borane reduction of ketones. The catalyst is derived from (2S,4R)-alpha,alpha-diphenyl-2-[(4-allyloxy)-N-benzyloxycarbonyl]pyrrolidinemethanol 3 and a methyl hydrosiloxane-dimethylsiloxane copolymer 4 (15% functionalized). Enantioselective reduction of prochiral ketones to the corresponding chiral alcohols proceeds with enantiomeric excesses up to 98%. The catalyst can be retained by a nanofiltration membrane and thus could be recovered after reaction or used in a continuously operated membrane reactor. (C) 1997 Elsevier Science Ltd.

引用

页码：1975 / 1977

页数：3

共 27 条

[1] Highly enantioenriched propargylic alcohols by oxazaborolidine-mediated reduction of acetylenic ketones [J].

Bach, J ;

Berenguer, R ;

Garcia, J ;

Loscertales, T ;

Vilarrasa, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :9021-9025

[2] SOME ENANTIOSELECTIVE BORANE REDUCTIONS OF PROCHIRAL KETONES CATALYZED BY POLYMER-SUPPORTED OXAZABOROLIDINES BOUND VIA THE BORON ATOM [J].

CAZE, C ;

ELMOUALIJ, N ;

HODGE, P ;

LOCK, CJ ;

MA, JB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (04) :345-349

[3] AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].

COREY, EJ ;

SHIBATA, S ;

BAKSHI, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863

[4] ENANTIOSELECTIVE AND PRACTICAL SYNTHESES OF R-FLUOXETINE AND S-FLUOXETINE [J].

COREY, EJ ;

REICHARD, GA .

TETRAHEDRON LETTERS, 1989, 30 (39) :5207-5210

[5] A NEW PROCESS FOR THE ENANTIOSELECTIVE SYNTHESIS OF CHIRAL ALPHA-ARYLOXY AND ALPHA-HYDROXY ACIDS [J].

COREY, EJ ;

LINK, JO .

TETRAHEDRON LETTERS, 1992, 33 (24) :3431-3434

[6] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[7] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[8] NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES [J].

COREY, EJ ;

HELAL, CJ .

TETRAHEDRON LETTERS, 1995, 36 (50) :9153-9156

[9] ASYMMETRIC BORON-CATALYZED REACTIONS [J].

DELOUX, L ;

SREBNIK, M .

CHEMICAL REVIEWS, 1993, 93 (02) :763-784

[10] THE ENANTIOSELECTIVE SYNTHESIS OF THE POTENT DOPAMINE D1 AGONIST (1R,3S)-3-(1'-ADAMANTYL)-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN (A77636) [J].

DENINNO, MP ;

PERNER, RJ ;

MORTON, HE ;

DIDOMENICO, S .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7115-7118

← 1 2 3 →