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ID 117188
Author
Wang, Yinli Tokushima University|Kyoto University
Yamauchi, Akiho Tokushima University
Hashimoto, Keiji Tokushima University
Fujiwara, Tatsuya Tokushima University
Mitani, Yuta Tokushima University
Kuwano, Satoru Kyoto University
Yamaoka, Yousuke Kyoto University
Takasu, Kiyosei Kyoto University
Keywords
organocatalysis
molecular recognition
catalytic kinetic resolution
α-hydroxythioamide
N-heterocyclic carbene
Content Type
Journal Article
Description
We describe a way of understanding enhanced molecular recognition through substrate–additive complex formation, and the development of the catalytic kinetic resolution of α-hydroxythioamides, which are versatile synthetic building blocks, using chiral N-heterocyclic carbine-catalyzed enantioselective acylation assisted by a carboxylate additive. Mass spectrometry provided evidence for the role of the additive, which forms a hydrogen-bonded complex with α-hydroxythioamide, resulting in both rate and selectivity enhancements. The synthetic applications of the resolved α-hydroxythioamides highlight the usefulness of the developed method.
Journal Title
ACS Catalysis
ISSN
21555435
NCID
AA12599706
Publisher
ACS Publications
Volume
12
Issue
10
Start Page
6100
End Page
6107
Published Date
2022-05-06
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.2c01579.
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DOI (Published Version)
URL ( Publisher's Version )
FullText File
language
eng
TextVersion
Author
departments
Pharmaceutical Sciences
Science and Technology