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ID 113939
Author
Kujime, Eiko Tokushima University|Matsuyama University
Tanaka, Hiroko Tokushima University
Keywords
Stereogenic phosphorus atom
Methyl bis(2,2,2-trifluoroethyl)phosphonoacetate
Horner-Wadsworth-Emmons reagent
Kinetic resolution
Enzymatic hydrolysis
Content Type
Journal Article
Description
In this data article, we describe the enzymatic kinetic resolution of a series of racemic mixed phosphonoacetates, which were successfully prepared from methyl bis(2,2,2-trifluoroethyl)phosphonoacetate (Still-Gennari reagent) by alcoholysis with σ-symmetrical secondary alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Porcine liver esterase (PLE)-catalyzed kinetic resolution of some of these racemic mixed phosphonoacetates proceeded in a highly stereoselective manner to furnish the chiral P-stereogenic phosphonoacetates (up to >99% ee).
Journal Title
Chemical Data Collections
ISSN
24058300
Publisher
Elsevier
Volume
5-6
Start Page
12
End Page
20
Published Date
2016-09-16
Rights
© 2016. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
EDB ID
DOI (Published Version)
URL ( Publisher's Version )
FullText File
language
eng
TextVersion
Author
departments
Pharmaceutical Sciences
Technical Support Department