Enhanced Molecular Recognition through Substrate–Additive Complex Formation in N‑Heterocyclic-Carbene-Catalyzed Kinetic Resolution of α‑Hydroxythioamides

We describe a new way of understanding enhanced molecular recognition through substrate–additive complex formation and the development of the first catalytic kinetic resolution of α-hydroxythioamides, which are versatile synthetic building blocks, using chiral N-heterocyclic carbene-catalyzed enanti...

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Bibliographic Details
Published in:ACS catalysis 2022-05, Vol.12 (10), p.6100-6107
Main Authors: Wang, Yinli, Yamauchi, Akiho, Hashimoto, Keiji, Fujiwara, Tatsuya, Inokuma, Tsubasa, Mitani, Yuta, Ute, Koichi, Kuwano, Satoru, Yamaoka, Yousuke, Takasu, Kiyosei, Yamada, Ken-ichi
Format: Article
Language:English
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Summary:We describe a new way of understanding enhanced molecular recognition through substrate–additive complex formation and the development of the first catalytic kinetic resolution of α-hydroxythioamides, which are versatile synthetic building blocks, using chiral N-heterocyclic carbene-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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.2c01579