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
catalytic kinetic resolution
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.
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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