Ynamide-Mediated Thionoester and Dithioester Syntheses
Abstract
A novel ynamide-mediated synthesis of thionoesters and dithioesters is described. The selective addition reactions of various monothiocarboxylic acids with ynamide furnish α-thioacyloxyenamides, which undergo transesterification with nucleophilic -OH or -SH species to afford thionoesters and dithioesters, respectively. The broad substrate scope, mild reaction conditions, and excellent yields make this method an attractive synthetic approach to thionoesters and dithioesters.
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Inspired by the design concept of ynamide coupling reagents, we have also developed a new class of racemization-free allenone coupling reagents for mediating peptide bond formation.
“Inspired by the design concept of ynamide coupling reagents, we have also developed a new class of racemization-free allenone coupling reagents for mediating peptide bond formation.57”
From Ynamide Coupling Reagents: Origin and Advances (2024) · cites this paper as [57]
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- Authors
- Yao, C., Yang, J., Lu, X., Zhang, S., & Zhao, J.
- Affiliations
- Jiangxi Normal University (CN)
- Corresponding author
- Zhao, Junfeng
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2020-08-11
- Volume
- 22
- Issue
- 16
- Pages
- 6628-6631
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W3048592716
- Cited by
- 35
- References
- 40
- Citations by year
- 2026: 1 · 2025: 9 · 2024: 6 · 2023: 5 · 2022: 8 · 2021: 5 · 2020: 1
- FWCI
- 1.84
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Organic Letters (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Natural Science Foundation of China (21762021, 91853114)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Reactivity of Sulfur-Containing Compounds
- Physical Sciences › Chemistry › Organic Chemistry › Sulfur-Based Synthesis Techniques
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Reactions
- Keywords
- ynamides, dithioesters, transesterification, nucleophilic addition, sulfur heterocycles
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