Biocatalytic Enantioselective Oxidative C-C Coupling by Aerobic C-H Activation

被引：58

作者：

Schrittwieser, Joerg H. ^{[1
]}

Resch, Verena ^{[1
]}

Sattler, Johann H. ^{[1
]}

Lienhart, Wolf-Dieter ^{[1
]}

Durchschein, Katharina ^{[1
]}

Winkler, Andreas ^{[2
]}

Gruber, Karl ^{[3
]}

Macheroux, Peter ^{[2
]}

Kroutil, Wolfgang ^{[1
]}

机构：

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

[2] Graz Univ Technol, Inst Biochem, A-8010 Graz, Austria

[3] Graz Univ, Inst Mol Biosci, A-8010 Graz, Austria

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 05期

基金：

奥地利科学基金会;

关键词：

alkaloids; asymmetric synthesis; C-C coupling; C-H activation; enzyme catalysis; BERBERINE BRIDGE ENZYME; ASYMMETRIC-SYNTHESIS; ISOQUINOLINE ALKALOIDS; TERMINAL ALKYNES; BENZYLISOQUINOLINE ALKALOIDS; CHEMOENZYMATIC SYNTHESIS; GREEN CHEMISTRY; HYDROGENATION; TETRAHYDROISOQUINOLINES; DIHYDROISOQUINOLINES;

D O I：

10.1002/anie.201006268

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bridging the gap: The berberine bridge enzyme (BBE) was employed for the first preparative oxidative biocatalytic C-C coupling that leads to a new intramolecular bond. This unique transformation requires O2 as sole stoichiometric oxidant and gives access to novel optically pure (S)-berbine 2 and (R)-1-benzyl-1,2,3,4-tetrahydroisoquinoline 1 alkaloid derivatives by kinetic resolution. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1068 / 1071

页数：4

共 67 条

[1]

[Anonymous], 2010, ANGEW CHEM

[2]

[Anonymous], BIOCATALYSIS PHARM B

[3]

[Anonymous], ANGEW CHEM

[4] Peroxidase-catalyzed coupling of solid-supported ortho-methox-lyphenols [J].

Antoniotti, S ;

Dordick, JS .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (7-8) :1119-1124

[5] Catalytic stereoselective benzylic C-H functionalizations by oxidative C-H activation and organocatalysis [J].

Benfatti, Fides ;

Capdevila, Montse Guiteras ;

Zoli, Luca ;

Benedetto, Elena ;

Cozzi, Pier Giorgio .

CHEMICAL COMMUNICATIONS, 2009, (39) :5919-5921

[6]

Bentley K.W., 1998, ISOQUINOLINE ALKALOI

[7] Palladium-Catalyzed Aerobic Oxidative Cross-Coupling Reactions of Terminal Alkynes with Alkylzinc Reagents [J].

Chen, Mao ;

Zheng, Xiaolong ;

Li, Wenqing ;

He, Jun ;

Lei, Aiwen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (12) :4101-+

[8] Asymmetric synthesis of isoquinoline alkaloids [J].

Chrzanowska, M ;

Rozwadowska, MD .

CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370

[9] MECHANISM OF THE CARDIOVASCULAR ACTIVITY OF LAUDANOSINE - COMPARISON WITH PAPAVERINE AND OTHER BENZYLISOQUINOLINES [J].

CHULIA, S ;

IVORRA, MD ;

LUGNIER, C ;

VILA, E ;

NOGUERA, MA ;

DOCON, P .

BRITISH JOURNAL OF PHARMACOLOGY, 1994, 113 (04) :1377-1385

[10] Recent progress in stereoselective synthesis with aldolases [J].

Clapes, Pere ;

Fessner, Wolf-Dieter ;

Sprenger, Georg A. ;

Samland, Anne K. .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (02) :154-167

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