Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)‐Catalyzed C−H Alkylation of Azacycles
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The development of new and practical 3‐pentoxythiocarbonyl auxiliaries for Ir I ‐catalyzed C−H alkylation of azacycles is described. This method allows for the α‐C−H alkylation of a variety of substituted pyrrolidines, piperidines, and tetrahydroisoquinolines through alkylation with alkenes. While the practicality of these simple carbamate‐type auxiliaries is underscored by the ease of installation and removal, the method's utility is demonstrated in its ability to functionalize biologically relevant l ‐proline and l ‐ trans ‐hydroxyproline, delivering unique 2,5‐dialkylated amino acid analogues that are not accessible by other C−H functionalization methods.
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Several of the enantiopure fragment recognition groups deployed herein are poised for direct modification using synthetic methodologies such as C-H bond activation chemistry.
“Toward this end, we note that the enantioprobes offer a convenient target engagement assay for assessing competitive binding of elaborated analogues in cells, and that several of the enantiopure fragment recognition groups deployed herein are poised for direct modification using synthetic methodologies such as C-H bond activation chemistry44–46.”
From Expedited mapping of the ligandable proteome using fully functionalized enantiomeric probe pairs (2019) · cites this paper as [45]
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Expedited mapping of the ligandable proteome using fully functionalized enantiomeric probe pairs
Wang, Y., Dix, M. M., Bianco, G., Remsberg, J. R., Lee, H.-Y., Kalocsay, M., Gygi, S. P., Forli, S., Vite, G., Lawrence, R. M., et al. (2019) · Nature Chemistry · doi:10.1038/s41557-019-0351-5 · Cited by 179 · see citing works
- Authors
- Tran, A. T., & Yu, J.
- Affiliations
- Scripps Research Institute (US)
- Corresponding author
- Yu, Jin‐Quan
- ORCID
- Yu, Jin‐Quan
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2017-07-24
- Volume
- 56
- Issue
- 35
- Pages
- 10530-10534
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- PMC
- PMC5561469
- OpenAlex
- W2625559439
- Cited by
- 105
- References
- 58
- Citations by year
- 2026: 4 · 2025: 8 · 2024: 5 · 2023: 6 · 2022: 14 · 2021: 15 · 2020: 15 · 2019: 16 · 2018: 18 · 2017: 4
- FWCI
- 6.05
- Type
- journal article
- Language
- en
- Open access
- green
- europepmc.org
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Institutes of Health (NIGMS, 2R01GM084019)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Catalytic C–H Functionalization Methods
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Catalytic Reactions
- Keywords
- iridium(I) catalysis, C–H alkylation, azacycles, pyrrolidine, piperidine, tetrahydroisoquinolines, alkene alkylation, proline, C–H functionalization
- MeSH terms
- Alkylation, Aza Compounds, Catalysis, Iridium, Isoquinolines, Organometallic Compounds, Piperidines, Pyrrolidines, Molecular Structure
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