Ynamides: Versatile Tools in Organic Synthesis
Abstract
Ynamides display an exceptionally fine balance between stability and reactivity. They also offer unique and multiple opportunities for the inclusion of nitrogen‐based functionalities into organic molecules, and are emerging as especially useful and versatile building blocks for organic synthesis. Recent breakthroughs in the preparation of these substrates have revitalized interest in nitrogen‐substituted alkynes, and the beginning of the 21st century has witnessed an ever‐increasing number of publications reporting the development of new reactions or synthetic sequences starting from ynamides. This Review highlights major developments in this area.
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Conventional coupling reagent-mediated head-to-tail cyclization of a linear peptide has inherent limitations, such as C-terminal epimerization, cyclodimerization, and formation of linear oligomers.
“However, the conventional coupling reagent-mediated head-to-tail cyclization of a linear peptide has inherent limitations, such as C-terminal epimerization, cyclodimerization, and formation of linear oligomers.36”
From Ynamide Coupling Reagents: Origin and Advances (2024) · cites this paper as [36]
Cites
Kanemura, S., Kondoh, A., Yasui, H., Yorimitsu, H., & Oshima, K. (2008) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.81.506 · Cited by 30 · see citing works
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Palladium-catalyzed hydroacyloxylation of ynamides
Smith, D. L., Goundry, W. R. F., & Lam, H. W. (2012) · Chem. Commun. · doi:10.1039/c1cc13595c · Cited by 95 · see citing works
Xu, S., Liu, J., Hu, D., & Bi, X. (2015) · Green Chemistry · doi:10.1039/c4gc01328j · Cited by 91 · see citing works
Ynamide Coupling Reagents: Origin and Advances
Hu, L., & Zhao, J. (2024) · Accounts of Chemical Research · doi:10.1021/acs.accounts.3c00743 · Cited by 89 · see citing works
Ynamide-Mediated Thionoester and Dithioester Syntheses
Yao, C., Yang, J., Lu, X., Zhang, S., & Zhao, J. (2020) · Organic Letters · doi:10.1021/acs.orglett.0c02402 · Cited by 35 · see citing works
- Authors
- Evano, G., Coste, A., & Jouvin, K.
- Affiliations
- Centre National de la Recherche Scientifique (FR)
- Corresponding author
- Evano, Gwilherm
- ORCID
- Evano, Gwilherm
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2010-03-30
- Volume
- 49
- Issue
- 16
- Pages
- 2840-2859
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2138790951
- Cited by
- 812
- References
- 1
- Citations by year
- 2026: 17 · 2025: 21 · 2024: 38 · 2023: 39 · 2022: 55 · 2021: 67 · 2020: 60 · 2019: 68 · 2018: 55 · 2017: 63 · 2016: 68 · 2015: 60 · 2014: 53 · 2013: 52 · 2012: 32
- FWCI
- 23.31
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Dépôt institutionnel de l'Université libre de Bruxelles (Université Libre de Bruxelles) (submittedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Catalytic Alkyne Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Synthetic Organic Chemistry
- Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
- Keywords
- ynamides, building blocks, organic synthesis
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