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

Baer, Katrin; Krausser, Marina; Burda, Edyta; Hummel, Werner; Berkessel, Albrecht; Gröger, Harald

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

Baer K, Krausser M, Burda E, Hummel W, Berkessel A, Gröger H (2009)
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 48(49): 9355-9358.

Zeitschriftenaufsatz | Veröffentlicht | Englisch

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DOI

https://doi.org/10.1002/anie.200900582

Autor*in

Baer, Katrin; Krausser, Marina; Burda, Edyta; Hummel, Werner; Berkessel, Albrecht; Gröger, Harald^UniBi

Einrichtung

Fakultät für Chemie > Industrielle Organische Chemie und Biotechnologie

Erscheinungsjahr

2009

Zeitschriftentitel

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Band

48

Ausgabe

49

Seite(n)

9355-9358

ISSN

1433-7851

eISSN

1521-3773

Page URI

https://pub.uni-bielefeld.de/record/2344823

Zitieren

Baer K, Krausser M, Burda E, Hummel W, Berkessel A, Gröger H. Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2009;48(49):9355-9358.

Baer, K., Krausser, M., Burda, E., Hummel, W., Berkessel, A., & Gröger, H. (2009). Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 48(49), 9355-9358. https://doi.org/10.1002/anie.200900582

Baer, Katrin, Krausser, Marina, Burda, Edyta, Hummel, Werner, Berkessel, Albrecht, and Gröger, Harald. 2009. “Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 48 (49): 9355-9358.

Baer, K., Krausser, M., Burda, E., Hummel, W., Berkessel, A., and Gröger, H. (2009). Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 48, 9355-9358.

Baer, K., et al., 2009. Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 48(49), p 9355-9358.

K. Baer, et al., “Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis”, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 48, 2009, pp. 9355-9358.

Baer, K., Krausser, M., Burda, E., Hummel, W., Berkessel, A., Gröger, H.: Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 48, 9355-9358 (2009).

Baer, Katrin, Krausser, Marina, Burda, Edyta, Hummel, Werner, Berkessel, Albrecht, and Gröger, Harald. “Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 48.49 (2009): 9355-9358.

14 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Reaction Mechanism of Organocatalytic Michael Addition of Nitromethane to Cinnamaldehyde: A Case Study on Catalyst Regeneration and Solvent Effects.
Świderek K, Nödling AR, Tsai YH, Luk LYP, Moliner V., J Phys Chem A 122(1), 2018
PMID: 29256614

Transition metal catalysis-a unique road map in the stereoselective synthesis of 1,3-polyols.
Kumar P, Tripathi D, Sharma BM, Dwivedi N., Org Biomol Chem 15(4), 2017
PMID: 27966714

Screening, Molecular Cloning, and Biochemical Characterization of an Alcohol Dehydrogenase from Pichia pastoris Useful for the Kinetic Resolution of a Racemic β-Hydroxy-β-trifluoromethyl Ketone.
Bulut D, Duangdee N, Gröger H, Berkessel A, Hummel W., Chembiochem 17(14), 2016
PMID: 27123855

From a Sequential to a Concurrent Reaction in Aqueous Medium: Ruthenium-Catalyzed Allylic Alcohol Isomerization and Asymmetric Bioreduction.
Ríos-Lombardía N, Vidal C, Liardo E, Morís F, García-Álvarez J, González-Sabín J., Angew Chem Int Ed Engl 55(30), 2016
PMID: 27258838

Cooperative catalysis of noncompatible catalysts through compartmentalization: wacker oxidation and enzymatic reduction in a one-pot process in aqueous media.
Sato H, Hummel W, Gröger H., Angew Chem Int Ed Engl 54(15), 2015
PMID: 25704961

Combining the 'two worlds' of chemocatalysis and biocatalysis towards multi-step one-pot processes in aqueous media.
Gröger H, Hummel W., Curr Opin Chem Biol 19(), 2014
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Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis.
Simon RC, Busto E, Schrittwieser JH, Sattler JH, Pietruszka J, Faber K, Kroutil W., Chem Commun (Camb) 50(99), 2014
PMID: 25251725

A mesoporous-silica-immobilized oxovanadium cocatalyst for the lipase-catalyzed dynamic kinetic resolution of racemic alcohols.
Egi M, Sugiyama K, Saneto M, Hanada R, Kato K, Akai S., Angew Chem Int Ed Engl 52(13), 2013
PMID: 23424181

Biocatalytic ketone reduction: a green and efficient access to enantiopure alcohols.
Ni Y, Xu JH., Biotechnol Adv 30(6), 2012
PMID: 22079798

One-pot chemoenzymatic synthesis of chiral 1,3-diols using an enantioselective aldol reaction with chiral Zn2+ complex catalysts and enzymatic reduction using oxidoreductases with cofactor regeneration.
Sonoike S, Itakura T, Kitamura M, Aoki S., Chem Asian J 7(1), 2012
PMID: 22174123

Recent progress in industrial biocatalysis.
Nestl BM, Nebel BA, Hauer B., Curr Opin Chem Biol 15(2), 2011
PMID: 21195018

Enantioselective double aldol reaction catalyzed by chiral phosphine oxide.
Shimoda Y, Kotani S, Sugiura M, Nakajima M., Chemistry 17(29), 2011
PMID: 21626594

Direction of kinetically versus thermodynamically controlled organocatalysis and its application in chemoenzymatic synthesis.
Rulli G, Duangdee N, Baer K, Hummel W, Berkessel A, Gröger H., Angew Chem Int Ed Engl 50(34), 2011
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A highly active and reusable self-assembled poly(imidazole/palladium) catalyst: allylic arylation/alkenylation.
Sarkar SM, Uozumi Y, Yamada YM., Angew Chem Int Ed Engl 50(40), 2011
PMID: 21948442

49 References

Daten bereitgestellt von Europe PubMed Central.

Kleemann, 2001

AUTHOR UNKNOWN, 0

Bode, Synthesis (), 2006

Binder, Chem. Commun. (), 2007

AUTHOR UNKNOWN, 2008

AUTHOR UNKNOWN, 0

Noyori, Angew. Chem. 113(), 2001

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 40(), 2001

Production of Lactobacillus kefir cells for asymmetric synthesis of a 3,5-dihydroxycarboxylate.
Pfruender H, Amidjojo M, Hang F, Weuster-Botz D., Appl. Microbiol. Biotechnol. 67(5), 2004
PMID: 15614560

Enzymatic resolution, desymmetrization, and dynamic kinetic asymmetric transformation of 1,3-cycloalkanediols.
Fransson AB, Xu Y, Leijondahl K, Backvall JE., J. Org. Chem. 71(17), 2006
PMID: 16901110

Kihumbu, Tetrahedron: Asymmetry 13(), 2002

AUTHOR UNKNOWN, 0

List, J. Am. Chem. Soc. 122(), 2000

Notz, J. Am. Chem. Soc. 122(), 2000

Pidathala, Angew. Chem. 115(), 2003

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 42(), 2003

Berkessel, Adv. Synth. Catal. 346(), 2004

Torii, Angew. Chem. 116(), 2004

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 43(), 2004

Hayashi, Angew. Chem. 118(), 2006

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 45(), 2006

Highly enantioselective direct aldol reaction catalyzed by organic molecules.
Raj M, Vishnumaya V, Ginotra SK, Singh VK., Org. Lett. 8(18), 2006
PMID: 16928083

Meciarova, Lett. Org. Chem. 3(), 2006

Amine-catalyzed direct aldol addition.
Markert M, Mulzer M, Schetter B, Mahrwald R., J. Am. Chem. Soc. 129(23), 2007
PMID: 17511461

Catalytic, asymmetric transannular aldolizations: total synthesis of (+)-hirsutene.
Chandler CL, List B., J. Am. Chem. Soc. 130(21), 2008
PMID: 18454521

Asymmetric enamine catalysis.
Mukherjee S, Yang JW, Hoffmann S, List B., Chem. Rev. 107(12), 2007
PMID: 18072803

Berkessel, 2005

AUTHOR UNKNOWN, 0

Kelly, J. Chem. Soc. Chem. Commun. (), 1991

Bertau, Tetrahedron: Asymmetry 12(), 2001

Systematic investigation of Saccharomyces cerevisiae enzymes catalyzing carbonyl reductions.
Kaluzna IA, Matsuda T, Sewell AK, Stewart JD., J. Am. Chem. Soc. 126(40), 2004
PMID: 15469278

Highly stereoselective reductions of alpha-alkyl-1,3-diketones and alpha-alkyl-beta-keto esters catalyzed by isolated NADPH-dependent ketoreductases.
Kalaitzakis D, Rozzell JD, Kambourakis S, Smonou I., Org. Lett. 7(22), 2005
PMID: 16235892

Kosjek, Tetrahedron: Asymmetry 17(), 2006

AUTHOR UNKNOWN, 0

Biocatalytic reductions: from lab curiosity to "first choice".
De Wildeman SM, Sonke T, Schoemaker HE, May O., Acc. Chem. Res. 40(12), 2007
PMID: 17941701

Buchholz, 2006

Liese, 2006

AUTHOR UNKNOWN, 0

Weckbecker, Biocatal. Biotransform. 24(), 2006

AUTHOR UNKNOWN, 0

Gais, 2002

AUTHOR UNKNOWN, 0

Combination of enzymes and metal catalysts. A powerful approach in asymmetric catalysis.
Pamies O, Backvall JE., Chem. Rev. 103(8), 2003
PMID: 12914497

AUTHOR UNKNOWN, 0

Chen, J. Org. Chem. 59(), 1994

Schoevaart, Tetrahedron Lett. 43(), 2002

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