Some studies involving the use of chiral amine oxides for the enantioselective preparation of (propargyl alcohol)Co2(CO)5(PR3) complexes

被引：9

作者：

Carpenter, NE ^{[1
]}

Nicholas, KM ^{[1
]}

机构：

[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA

来源：

POLYHEDRON | 1999年 / 18卷 / 15期

关键词：

chiral amine oxide; enantioselective preparation; (propargyl alcohol)Co-2(CO)(5)(PR3) complexes;

D O I：

10.1016/S0277-5387(99)00077-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective preparation of (propargyl alcohol) dicobalt pentacarbonylphosphine complexes (2) via kinetic resolution with an optically active amine oxide was examined. Variations in temperature, solvent, phosphine, amine oxide, and substrate were studied. Diastereoselectivity showed marked improvement over thermal methods, while enantioselectivity was modest. The typical e.e. for product 2a was 20% at 30-40% conversion when the reaction was carried out at -58 degrees C in a 1:1 mixture of tetrahydrofuran/dichloromethane with brucine N-oxide as the promoter. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2027 / 2034

页数：8

共 30 条

[1] REAGENT AND CATALYST INDUCED SUBSTITUTION-REACTIONS OF METAL-CARBONYL-COMPLEXES [J].

ALBERS, MO ;

COVILLE, NJ .

COORDINATION CHEMISTRY REVIEWS, 1984, 53 (JAN) :227-259

[2] ENZYMATIC RESOLUTION OF A CHIRAL ORGANOMETALLIC ESTER - ENANTIOSELECTIVE HYDROLYSIS OF 2-ETHOXYCARBONYLBUTA-1,3-DIENETRICARBONYLIRON BY PIG-LIVER ESTERASE [J].

ALCOCK, NW ;

CROUT, DHG ;

HENDERSON, CM ;

THOMAS, SE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (11) :746-747

[3] METAL CARBONYLS .1. CARBON MONOXIDE EXCHANGE WITH NICKEL TETRACARBONYL AND DICOBALT OCTACARBONYL [J].

BASOLO, F ;

WOJCICKI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (03) :520-+

[4] NOVEL-APPROACH TO OPTICALLY-ACTIVE ENONE IRON CARBONYL-COMPLEXES - CORRELATION BETWEEN THEIR ABSOLUTE-CONFIGURATION AND CIRCULAR-DICHROISM [J].

BENDER, BR ;

KOLLER, M ;

LINDEN, A ;

MARCUZZI, A ;

VONPHILIPSBORN, W .

ORGANOMETALLICS, 1992, 11 (12) :4268-4275

[5] PREPARATION, SOLUTION STRUCTURES, AND NUCLEOPHILIC REACTIONS OF CHIRAL, BIMETALLIC COMPLEXES - [(MU-ETA-2,ETA-3-PROPARGYLIUM)CO2(CO)5P(C6H5)3]BF4 [J].

BRADLEY, DH ;

KHAN, MA ;

NICHOLAS, KM .

ORGANOMETALLICS, 1992, 11 (07) :2598-2607

[6] DIASTEREOSELECTIVE SYNTHESIS OF CHIRAL CLUSTERS FROM THE REACTION OF CHIRAL (PROPARGYL ALCOHOL)CO2(CO)6 WITH TRIPHENYLPHOSPHINE [J].

BRADLEY, DH ;

KHAN, MA ;

NICHOLAS, KM .

ORGANOMETALLICS, 1989, 8 (02) :554-556

[7]

BRADLEY DH, 1992, THESIS U OKLAHOMA

[8] OPTICALLY-ACTIVE TRANSITION-METAL COMPLEXES .102. ENANTIOSELECTIVE SYNTHESIS OF 3-OXABICYCLO[3.3.0]OCT-7-EN-7-PHENYL-6-ON VIA KHAND-PAUSON REACTION [J].

BRUNNER, H ;

NIEDERNHUBER, A .

TETRAHEDRON-ASYMMETRY, 1990, 1 (10) :711-714

[9] STEREOSELECTIVE PROPARGYLATION MEDIATED BY A CHIRAL METAL CLUSTER - REACTIONS OF [(PROPARGYLIUM)CO2(CO)5-(P(OR)3)][BF4] WITH CARBON NUCLEOPHILES [J].

CAFFYN, AJM ;

NICHOLAS, KM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6438-6439

[10]

CAFFYN AJM, 1995, COMPREHENSIVE ORGANO, V12

← 1 2 3 →