Dynamic Kinetic Resolution of Racemic β-Haloalcohols: Direct Access to Enantioenriched Epoxides

The direct chemo-enzymatic DKR of racemic β-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 h...

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Published in:Journal of the American Chemical Society 2008-10, Vol.130 (41), p.13508-13509
Main Authors: Haak, Robert M, Berthiol, Florian, Jerphagnon, Thomas, Gayet, Arnaud J. A, Tarabiono, Chiara, Postema, Christiaan P, Ritleng, Vincent, Pfeffer, Michel, Janssen, Dick B, Minnaard, Adriaan J, Feringa, Ben L, de Vries, Johannes G
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Catalysis
Chemical Sciences
Cyclization
Epoxy Compounds - chemistry
Halogens - chemistry
Kinetics
Molecular Structure
Stereoisomerism
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cited_by cdi_FETCH-LOGICAL-a385t-fa2ceca8f51ae67638399ff936ed7b9a76daecd10ee854fe5313be0e9fee18603
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container_end_page 13509
container_issue 41
container_start_page 13508
container_title Journal of the American Chemical Society
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creator Haak, Robert M
Berthiol, Florian
Jerphagnon, Thomas
Gayet, Arnaud J. A
Tarabiono, Chiara
Postema, Christiaan P
Ritleng, Vincent
Pfeffer, Michel
Janssen, Dick B
Minnaard, Adriaan J
Feringa, Ben L
de Vries, Johannes G
description The direct chemo-enzymatic DKR of racemic β-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 β-haloalcohols.
doi_str_mv 10.1021/ja805128x
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Alcohols - chemistry
Catalysis
Chemical Sciences
Cyclization
Epoxy Compounds - chemistry
Halogens - chemistry
Kinetics
Molecular Structure
Stereoisomerism
title Dynamic Kinetic Resolution of Racemic β-Haloalcohols: Direct Access to Enantioenriched Epoxides
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