Tandem Concurrent Processes: One-Pot Single-Catalyst Biohydrogen Transfer for the Simultaneous Preparation of Enantiopure Secondary Alcohols

被引：58

作者：

Bisogno, Fabricio R. ^{[1
]}

Lavandera, Ivan ^{[1
]}

Kroutil, Wolfgang ^{[2
]}

Gotor, Vicente ^{[1
]}

机构：

[1] Univ Oviedo, Dept Quim Organ & Inorgan, Inst Univ Biotechnol Asturias, E-33006 Oviedo, Spain

[2] Graz Univ, Dept Chem Organ & Bioorgan Chem, A-8010 Graz, Austria

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 04期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; CHIRAL ALCOHOLS; SEC-ALCOHOLS; REDUCTION; KETONES; OXIDATION; DEHYDROGENASE; EFFICIENCY;

D O I：

10.1021/jo802350f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel one-pot tandem biohydrogen transfer process to concurrently obtain two enantiopure sec-alcohols is presented; thus, using a suitable single enzyme and a catalytic amount of cofactor, several interesting building blocks could be easily achieved in an enantiocomplementary fashion, minimizing dramatically the quantity of reagents usually employed in the "coupled-substrate" approach.

引用

页码：1730 / 1732

页数：3

共 34 条

[1]

ARENDS IWC, 2007, CATALYTIC OXIDATIONS

[2]

Backvall J.-E., 2004, Modern Oxidation Methods

[3] Industrial methods for the production of optically active intermediates [J].

Breuer, M ;

Ditrich, K ;

Habicher, T ;

Hauer, B ;

Kesseler, M ;

Stürmer, R ;

Zelinski, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) :788-824

[4] Biocatalytic reductions: From lab curiosity to "first choice" [J].

De Wildeman, Stefaan M. A. ;

Sonke, Theo ;

Schoemaker, Hants E. ;

May, Oliver .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1260-1266

[5] Maximise equilibrium conversion in biphasic catalysed reactions: Mathematical description and practical guideline [J].

Eckstein, Marrit F. ;

Peters, Martina ;

Lembrecht, Julia ;

Spiess, Antje C. ;

Greiner, Lasse .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) :1591-1596

[6] Biocatalytic deuterium- and hydrogen-transfer using over-expressed ADH-'A':: enhanced stereoselectivity and 2H-labeled chiral alcohols [J].

Edegger, Klaus ;

Gruber, Christian C. ;

Poessl, Tina M. ;

Wallner, Sabine R. ;

Lavandera, Ivan ;

Faber, Kurt ;

Niehaus, Frank ;

Eck, Juergen ;

Oehrlein, Reinhold ;

Hafner, Andreas ;

Kroutil, Wolfgang .

CHEMICAL COMMUNICATIONS, 2006, (22) :2402-2404

[7] Kinetic modeling of acetophenone reduction catalyzed by alcohol dehydrogenase from Thermoanaerobacter sp. [J].

Findrik, Z ;

Vasic-Racki, D ;

Lütz, S ;

Daussmann, T ;

Wandrey, C .

BIOTECHNOLOGY LETTERS, 2005, 27 (15) :1087-1095

[8] Asymmetric transfer hydrogenation: chiral ligands and applications [J].

Gladiali, S ;

Alberico, E .

CHEMICAL SOCIETY REVIEWS, 2006, 35 (03) :226-236

[9] Biocatalytic ketone reduction -: a powerful tool for the production of chiral alcohols -: part I:: processes with isolated enzymes [J].

Goldberg, Katja ;

Schroer, Kirsten ;

Luetz, Stephan ;

Liese, Andreas .

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2007, 76 (02) :237-248

[10] Intramolecular hydrogen bonding in chiral alcohols: The microwave spectrum of the chloropropanols [J].

Goldstein, T ;

Snow, MS ;

Howard, BJ .

JOURNAL OF MOLECULAR SPECTROSCOPY, 2006, 236 (01) :1-10

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