Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis

被引：108

作者：

Baer, Katrin ^{[1
]}

Krausser, Marina ^{[1
]}

Burda, Edyta ^{[1
]}

Hummel, Werner ^{[2
]}

Berkessel, Albrecht ^{[3
]}

Groeger, Harald ^{[1
]}

机构：

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

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

[3] Univ Cologne, Dept Chem, D-50939 Cologne, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 49期

关键词：

alcohols; aldol reactions; asymmetric catalysis; biocatalysis; organocatalysis; STEREOSELECTIVE-SYNTHESIS; ALDOL REACTIONS; ALCOHOL-DEHYDROGENASE; ASYMMETRIC CATALYSIS; LACTOBACILLUS-KEFIR; ALDOLIZATIONS; REDUCTIONS; RESOLUTION; WATER;

D O I：

10.1002/anie.200900582

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chemical Equitation Presentation Biocompatible: A modular chemoenzymatic synthesis (see scheme) based on asymmetric organo- and biocatalytic reaction sequences allows the sequential construction of both stereogenic centers of 1,3-diols and leads to all four possible stereoisomers in enantiomerically pure form. The biocompatibility of the organocatalytic aldol reaction allows its direct use in the subsequent enzymatic reduction without the need for a work-up step. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：9355 / 9358

页数：4

共 38 条

[1] Proline-derived N-sullfonylcarboxamides:: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions [J].

Berkessel, A ;

Koch, B ;

Lex, J .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1141-1146

[2]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[3] A novel highly stereoselective synthesis of chiral 5-and 4,5-substituted 2-oxazolidinones [J].

Bertau, M ;

Bürli, M ;

Hungerbühler, E ;

Wagner, P .

TETRAHEDRON-ASYMMETRY, 2001, 12 (15) :2103-2107

[4] Iterative approach to polyketide-type structures: stereoselective synthesis of 1,3-polyols utilizing the catalytic asymmetric Overman esterification [J].

Binder, Joerg T. ;

Kirsch, Stefan F. .

CHEMICAL COMMUNICATIONS, 2007, (40) :4164-4166

[5] Stereoselective synthesis of 1,3-diols [J].

Bode, SE ;

Wolberg, M ;

Müller, M .

SYNTHESIS-STUTTGART, 2006, (04) :557-588

[6]

Borner A., 2008, PHOSPHORUS LIGANDS A, V1-3

[7]

BUCHHOLZ S, 2006, BIOCATALYSIS PHARM B, P757

[8] Catalytic, asymmetric transannular aldolizations: Total synthesis of (+)-hirsutene [J].

Chandler, Carley L. ;

List, Benjamin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (21) :6737-+

[9] RESOLUTION OF AMINO-ACIDS IN A MIXTURE OF 2-METHYL-2-PROPANOL WATER (19/1) CATALYZED BY ALCALASE VIA IN-SITU RACEMIZATION OF ONE ANTIPODE MEDIATED BY PYRIDOXAL 5-PHOSPHATE [J].

CHEN, ST ;

HUANG, WH ;

WANG, KT .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7580-7581

[10] 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

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