Literature DB >> 18800793

Dynamic kinetic resolution of racemic beta-haloalcohols: direct access to enantioenriched epoxides.

Robert M Haak1, Florian Berthiol, Thomas Jerphagnon, Arnaud J A Gayet, Chiara Tarabiono, Christiaan P Postema, Vincent Ritleng, Michel Pfeffer, Dick B Janssen, Adriaan J Minnaard, Ben L Feringa, Johannes G de Vries.   

Abstract

The direct chemo-enzymatic DKR of racemic beta-haloalcohols is reported, yielding the corresponding optically active epoxides in a single step. The mutant haloalcohol dehalogenase HheC Cys153Ser Trp249Phe is used for the asymmetric ring closure, whereas racemization of the remaining enantiomer of the haloalcohol is achieved using the new iridacycle 3, one of the most effective racemization catalysts to date for beta-haloalcohols.

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Year:  2008        PMID: 18800793     DOI: 10.1021/ja805128x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  12 in total

1.  Synthetic cascades are enabled by combining biocatalysts with artificial metalloenzymes.

Authors:  V Köhler; Y M Wilson; M Dürrenberger; D Ghislieri; E Churakova; T Quinto; L Knörr; D Häussinger; F Hollmann; N J Turner; T R Ward
Journal:  Nat Chem       Date:  2012-11-25       Impact factor: 24.427

2.  Expanding the Halohydrin Dehalogenase Enzyme Family: Identification of Novel Enzymes by Database Mining.

Authors:  Marcus Schallmey; Julia Koopmeiners; Elizabeth Wells; Rainer Wardenga; Anett Schallmey
Journal:  Appl Environ Microbiol       Date:  2014-09-19       Impact factor: 4.792

3.  Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols.

Authors:  Kun Huang; Haiyang Wang; Viatcheslav Stepanenko; Melvin De Jesús; Carilyn Torruellas; Wildeliz Correa; Margarita Ortiz-Marciales
Journal:  J Org Chem       Date:  2011-02-04       Impact factor: 4.354

4.  Expression, characterization, and improvement of a newly cloned halohydrin dehalogenase from Agrobacterium tumefaciens and its application in production of epichlorohydrin.

Authors:  Zhi-Qiang Liu; Ai-Cun Gao; Ya-Jun Wang; Yu-Guo Zheng; Yin-Chu Shen
Journal:  J Ind Microbiol Biotechnol       Date:  2014-04-29       Impact factor: 3.346

5.  Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of α-keto esters.

Authors:  Kimberly M Steward; Michael T Corbett; C Guy Goodman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419

Review 6.  Chemoenzymatic dynamic kinetic resolution: a powerful tool for the preparation of enantiomerically pure alcohols and amines.

Authors:  Oscar Verho; Jan-E Bäckvall
Journal:  J Am Chem Soc       Date:  2015-03-19       Impact factor: 15.419

7.  Aromatic alkyne insertion into six-membered cyclometalated pyridine complexes of iridium: different insertion modes and structurally novel products.

Authors:  Xiaodan Chu; Shaowei Zhang; Zhuo Wang; Tongyu Li; Bolin Zhu
Journal:  RSC Adv       Date:  2018-02-14       Impact factor: 3.361

8.  Synthesis of thioethers, arenes and arylated benzoxazoles by transformation of the C(aryl)-C bond of aryl alcohols.

Authors:  Mingyang Liu; Zhanrong Zhang; Bingfeng Chen; Qinglei Meng; Pei Zhang; Jinliang Song; Buxing Han
Journal:  Chem Sci       Date:  2020-04-15       Impact factor: 9.825

9.  Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network.

Authors:  Xingwei Guo; Yasunori Okamoto; Mirjam R Schreier; Thomas R Ward; Oliver S Wenger
Journal:  Chem Sci       Date:  2018-05-17       Impact factor: 9.825

10.  Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts.

Authors:  Jan Seliger; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2020-10-27       Impact factor: 15.336

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