Efficient ruthenium-catalyzed racemization of secondary alcohols: application to dynamic kinetic resolution

被引：76

作者：

Dijksman, A ^{[1
]}

Elzinga, JM ^{[1
]}

Li, YX ^{[1
]}

Arends, IWCE ^{[1
]}

Sheldon, RA ^{[1
]}

机构：

[1] Delft Univ Technol, Dept Biotechnol, NL-2628 BL Delft, Netherlands

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(02)00187-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Three new ruthenium-based catalytic systems are described which are capable of catalyzing the racemization of chiral secondary alcohols. In addition, one of these systems, [TosN(CH2)(2)NH2]RuCl(p-cymene)/TEMPO, was able to catalyze the in Situ racemization during enzymatic resolution, i.e. dynamic kinetic resolution. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：879 / 884

页数：6

共 33 条

[1] Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones: Mechanism and origin of enantioselectivity [J].

Alonso, DA ;

Brandt, P ;

Nordin, SJM ;

Andersson, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9580-9588

[2] 2-azanorbornyl alcohols: Very efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones [J].

Alonso, DA ;

Nordin, SJM ;

Roth, P ;

Tarnai, T ;

Andersson, PG ;

Thommen, M ;

Pittelkow, U .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3116-3122

[3] Evidence for a ruthenium dihydride species as the active catalyst in the RuCl2(PPh3)-catalyzed hydrogen transfer reaction in the presence of base [J].

Aranyos, A ;

Csjernyik, G ;

Szabó, KJ ;

Bäckvall, JE .

CHEMICAL COMMUNICATIONS, 1999, (04) :351-352

[4] Highly enantioselective aminoacylase-catalyzed transesterification of secondary alcohols [J].

Bakker, M ;

Spruijt, AS ;

van Rantwijk, F ;

Sheldon, RA .

TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1801-1808

[5] (ETA-6-HEXAMETHYLBENZENE)RUTHENIUM COMPLEXES [J].

BENNETT, MA ;

HUANG, TN ;

MATHESON, TW ;

SMITH, AK .

INORGANIC SYNTHESES, 1982, 21 :74-78

[6] Efficient ruthenium-TEMPO-catalysed aerobic oxidation of aliphatic alcohols into aldehydes and ketones [J].

Dijksman, A ;

Arends, IWCE ;

Sheldon, RA .

CHEMICAL COMMUNICATIONS, 1999, (16) :1591-1592

[7] Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium/TEMPO as the catalytic system [J].

Dijksman, A ;

Marino-González, A ;

Payeras, AMI ;

Arends, IWCE ;

Sheldon, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6826-6833

[8] Catalytic racemisation of alcohols: Applications to enzymatic resolution reactions [J].

Dinh, PM ;

Howarth, JA ;

Hudnott, AR ;

Williams, JMJ ;

Harris, W .

TETRAHEDRON LETTERS, 1996, 37 (42) :7623-7626

[9]

Doucet H, 1998, ANGEW CHEM INT EDIT, V37, P1703, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1703::AID-ANIE1703>3.0.CO

[10]

2-I

← 1 2 3 4 →