Ruthenium and enzyme-catalyzed dynamic kinetic resolution of alcohols

被引：27

作者：

Karvembu, R. ^{[1
]}

Prabhakaran, R. ^{[2
]}

Tamizh, M. Muthu ^{[1
]}

Natarajan, K. ^{[2
]}

机构：

[1] Natl Inst Technol, Dept Chem, Tiruchirappalli 620015, Tamil Nadu, India

[2] Bharathiar Univ, Dept Chem, Coimbatore 641046, Tamil Nadu, India

来源：

COMPTES RENDUS CHIMIE | 2009年 / 12卷 / 09期

关键词：

Ruthenium; Racemization; Dynamic kinetic resolution; Chiral; OPPENAUER-TYPE OXIDATION; SECONDARY ALCOHOLS; ASYMMETRIC TRANSFORMATIONS; RACEMIZATION CATALYSTS; ENANTIOSELECTIVE SYNTHESIS; ENOL ACETATES; METAL; KETONES; COMBINATION; COMPLEXES;

D O I：

10.1016/j.crci.2008.09.002

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ruthenium acts as a good catalyst for the racemization reaction of secondary alcohols and amines. Ruthenium-catalyzed racemization is coupled with enzymatic kinetic resolution to prepare chiral compounds in 100% theoretical yield. Ten ruthenium complexes (1-10) act as a good catalyst the for racemization reaction and are also compatible with DKR process. Two other ruthenium complexes [RuCl2(PPh3)(3)] and [Cp*RuCl(COD)] are active for racemization reaction but their successful compatibility with DKR has not yet been reported. Ru/gamma-Al2O3 and Ru-HAP are the heterogeneous catalysts used for the racemization reaction. They have also not been employed for DKR process. Polymer supported ruthenium is employed as a reusable racemization catalyst for aerobic DKR of alcohols. To cite this article: R. Karvembu et al., C R. Chimie 12 (2009). (C) 2008 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.

引用

页码：951 / 962

页数：12

共 53 条

[1] Racemization catalysts for the dynamic kinetic resolution of alcohols and amines [J].

Ahn, Yangsoo ;

Ko, Soo-Byung ;

Kim, Mahn-Joo ;

Park, Jaiwook .

COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :647-658

[2] Ruthenium(II)-catalyzed Oppenauer-type oxidation of secondary alcohols [J].

Almeida, MLS ;

Beller, M ;

Wang, GZ ;

Backvall, JE .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (12) :1533-1536

[3] Ruthenium-catalyzed Oppenauer-type oxidation of 3 beta-hydroxy steroids. A highly efficient entry into the steroidal hormones with 4-en-3-one functionality [J].

Almeida, MLS ;

Kocovsky, P ;

Backvall, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6587-6590

[4] RUTHENIUM-CATALYZED ISOMERIZATION OF ALLYLIC ALCOHOLS TO SATURATED KETONES [J].

BACKVALL, JE ;

ANDREASSON, U .

TETRAHEDRON LETTERS, 1993, 34 (34) :5459-5462

[5]

Borman S, 2002, CHEM ENG NEWS, V80, P43, DOI 10.1021/cen-v080n003.p043

[6] Aminocyclopentadienyl ruthenium complexes as racemization catalysts for dynamic kinetic resolution of secondary alcohols at ambient temperature [J].

Choi, JH ;

Choi, YK ;

Kim, YH ;

Park, ES ;

Kim, EJ ;

Kim, MJ ;

Park, JW .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :1972-1977

[7]

Choi JH, 2002, ANGEW CHEM INT EDIT, V41, P2373, DOI 10.1002/1521-3773(20020703)41:13<2373::AID-ANIE2373>3.0.CO

[8]

2-7

[9] EFFICIENT RUTHENIUM-CATALYZED TRANSFER HYDROGENATION OF KETONES BY PROPAN-2-OL [J].

CHOWDHURY, RL ;

BACKVALL, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (16) :1063-1064

[10] Efficient ruthenium-catalyzed racemization of secondary alcohols: application to dynamic kinetic resolution [J].

Dijksman, A ;

Elzinga, JM ;

Li, YX ;

Arends, IWCE ;

Sheldon, RA .

TETRAHEDRON-ASYMMETRY, 2002, 13 (08) :879-884

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