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Chemoenzymatic Deracemization of Secondary Alcohols by using a TEMPO-Iodine-Alcohol Dehydrogenase System

Mendez-Sanchez, Daniel; Mangas, Juan LU ; Lavandera, Ivan; Gotor, Vicente and Gotor-Fernandez, Vicente (2015) In ChemCatChem 7(24). p.4016-4020
Abstract
A deracemization system for secondary alcohols was established after the analysis of individual steps and their compatibility in one pot. The chemical oxidation and bioreduction occurred in a sequential manner to yield 1-arylethanols and lineal aliphatic alcohols with excellent conversions and enantiomeric excess values. The oxidation step was performed by using 2,2,6,6-tetramethylpiperidin-1-oxyl and iodine. This chemical process was extremely favored by sonication, which allowed quantitative formation of the corresponding ketone intermediates after just 1h. Simple destruction of iodine in the same pot allowed sequential bioreduction of the ketones by using either Prelog or antiPrelog enzymes, which led to the preparation of the... (More)
A deracemization system for secondary alcohols was established after the analysis of individual steps and their compatibility in one pot. The chemical oxidation and bioreduction occurred in a sequential manner to yield 1-arylethanols and lineal aliphatic alcohols with excellent conversions and enantiomeric excess values. The oxidation step was performed by using 2,2,6,6-tetramethylpiperidin-1-oxyl and iodine. This chemical process was extremely favored by sonication, which allowed quantitative formation of the corresponding ketone intermediates after just 1h. Simple destruction of iodine in the same pot allowed sequential bioreduction of the ketones by using either Prelog or antiPrelog enzymes, which led to the preparation of the enantiopure alcohols in excellent yields. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
alcohols, biocatalysis, deracemization, oxidoreductases, TEMPO
in
ChemCatChem
volume
7
issue
24
pages
4016 - 4020
publisher
John Wiley & Sons
external identifiers
  • wos:000366838200003
  • scopus:84950311274
ISSN
1867-3880
DOI
10.1002/cctc.201500816
language
English
LU publication?
yes
id
c3e5b5af-0f05-43bb-828d-eaa6826cf876 (old id 8542837)
date added to LUP
2016-01-29 12:00:57
date last changed
2017-01-01 03:00:42
@article{c3e5b5af-0f05-43bb-828d-eaa6826cf876,
  abstract     = {A deracemization system for secondary alcohols was established after the analysis of individual steps and their compatibility in one pot. The chemical oxidation and bioreduction occurred in a sequential manner to yield 1-arylethanols and lineal aliphatic alcohols with excellent conversions and enantiomeric excess values. The oxidation step was performed by using 2,2,6,6-tetramethylpiperidin-1-oxyl and iodine. This chemical process was extremely favored by sonication, which allowed quantitative formation of the corresponding ketone intermediates after just 1h. Simple destruction of iodine in the same pot allowed sequential bioreduction of the ketones by using either Prelog or antiPrelog enzymes, which led to the preparation of the enantiopure alcohols in excellent yields.},
  author       = {Mendez-Sanchez, Daniel and Mangas, Juan and Lavandera, Ivan and Gotor, Vicente and Gotor-Fernandez, Vicente},
  issn         = {1867-3880},
  keyword      = {alcohols,biocatalysis,deracemization,oxidoreductases,TEMPO},
  language     = {eng},
  number       = {24},
  pages        = {4016--4020},
  publisher    = {John Wiley & Sons},
  series       = {ChemCatChem},
  title        = {Chemoenzymatic Deracemization of Secondary Alcohols by using a TEMPO-Iodine-Alcohol Dehydrogenase System},
  url          = {http://dx.doi.org/10.1002/cctc.201500816},
  volume       = {7},
  year         = {2015},
}