Formal Asymmetric Hydration of Non-Activated Alkenes in Aqueous Medium through a "Chemoenzymatic Catalytic System"

被引：49

作者：

Schnapperelle, Ingo ^{[1
]}

Hummel, Werner ^{[2
]}

Groeger, Harald ^{[1
]}

机构：

[1] Univ Erlangen Nurnberg, Dept Chem & Pharm, D-91054 Erlangen, Germany

[2] Univ Dusseldorf, Inst Mol Enzyme Technol, Forschungszentrum Julich, D-52426 Julich, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 04期

关键词：

alcohols; asymmetric hydration; enzyme catalysis; palladium; synthetic methods; OXIDATION; OLEFINS;

D O I：

10.1002/chem.201102579

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct one-pot conversion of (substituted) styrene(s) into the corresponding (substituted) (R)-phenylethan-1-ol(s) in a highly enantioselective manner has been achieved by using a "chemoenzymatic catalytic system", comprising a palladium-catalyzed Wacker-Tsuji oxidation and subsequent enantioselective enzymatic reduction of the in situ formed (substituted) acetophenone(s) (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1073 / 1076

页数：4

共 12 条

[1]

[Anonymous], 2010, CATALYTIC ASYMMETRIC

[2]

Groger H., 2010, Encyclopedia of Industrial Biotechnology. Bioprocess, Bioseparation, V3, P2094

[3]

Helmchen G., 2000, HOUBEN WEYL METHOD E, VE21

[4] Recent Developments in Metal-Catalyzed Additions of Oxygen Nucleophiles to Alkenes and Alkynes [J].

Hintermann, Lukas .

C-X BOND FORMATION, 2010, 31 :123-155

[5] The selective addition of water to C=C bonds; enzymes are the best chemists [J].

Jin, Jianfeng ;

Hanefeld, Ulf .

CHEMICAL COMMUNICATIONS, 2011, 47 (09) :2502-2510

[6] MhyADH catalysed Michael addition of water and in situ oxidation [J].

Jin, Jianfeng ;

Oskam, Philip C. ;

Karmee, Sanjib K. ;

Straathof, Adrie J. J. ;

Hanefeld, Ulf .

CHEMICAL COMMUNICATIONS, 2010, 46 (45) :8588-8590

[7] Enantioselective hydroboration of olefins catalysed by cationic rhodium complexes of 2-phenylquinazolin-4-yl-2-(diphenylphosphino)naphthalene [J].

McCarthy, M ;

Hooper, MW ;

Guiry, PJ .

CHEMICAL COMMUNICATIONS, 2000, (14) :1333-1334

[8] Complexometric determination of palladium(II) using thioacetamide as a selective masking agent [J].

Parameshwara, P ;

Karthikeyan, J ;

Shetty, AN ;

Shetty, P .

ANNALI DI CHIMICA, 2006, 96 (1-2) :125-129

[9] SPECTROPHOTOMETRIC DETERMINATION OF GLUTATHIONE AND OF ITS OXIDATION-PRODUCT IN PHARMACEUTICAL DOSAGE FORMS [J].

RAGGI, MA ;

NOBILE, L ;

GIOVANNINI, AG .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1991, 9 (10-12) :1037-1040

[10]

TSUJI J, 1984, SYNTHESIS-STUTTGART, P369

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