Isothiourea‐Catalysed Acylative Kinetic and Dynamic Kinetic Resolution of Planar Chiral Paracyclophanols Article Swipe
Andrew D. Smith
,
Zhanyu Zhou
,
Kevin Kasten
,
Aidan P. McKay
,
David B. Cordes
·
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1002/anie.202507126
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1002/anie.202507126
The development of synthetic methods for the catalytic enantioselective preparation of planar chiral paracyclophane derivatives is of considerable interest to the synthetic community. To date, relatively few successful and effective organocatalytic approaches to this molecular class have been reported. This manuscript describes effective isothiourea catalysed acylative kinetic (KR) and dynamic kinetic resolution (DKR) approaches to the generation of a range of planar chiral paracyclophane macrocycles with excellent levels of enantioselectivity. Effective KR of configurationally stable planar chiral paracyclophanols with 12‐ and 13‐membered ansa ‐chains is demonstrated (6 examples, s = up to 50) using 5 mol% of the isothiourea ( R )‐BTM and isobutyric anhydride. Application to configurationally labile macrocyclic phenols with 14 to 18‐membered ansa ‐chains allows their effective acylative DKR, generating the desired products with excellent enantioselectivity (25 examples, up to 95% yield and 98:2 er).
Related Topics
Concepts
Kinetic resolution
Enantioselective synthesis
Chemistry
Planar
Yield (engineering)
Catalysis
Context (archaeology)
Combinatorial chemistry
Kinetic energy
Phenols
Organic chemistry
Computational chemistry
Materials science
Computer science
Physics
Biology
Quantum mechanics
Computer graphics (images)
Metallurgy
Paleontology
Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1002/anie.202507126
- https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/anie.202507126
- OA Status
- hybrid
- Cited By
- 1
- References
- 183
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4410539114
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4410539114Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1002/anie.202507126Digital Object Identifier
- Title
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Isothiourea‐Catalysed Acylative Kinetic and Dynamic Kinetic Resolution of Planar Chiral ParacyclophanolsWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
-
2025Year of publication
- Publication date
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2025-05-20Full publication date if available
- Authors
-
Andrew D. Smith, Zhanyu Zhou, Kevin Kasten, Aidan P. McKay, David B. CordesList of authors in order
- Landing page
-
https://doi.org/10.1002/anie.202507126Publisher landing page
- PDF URL
-
https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/anie.202507126Direct link to full text PDF
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YesWhether a free full text is available
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hybridOpen access status per OpenAlex
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https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/anie.202507126Direct OA link when available
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Kinetic resolution, Enantioselective synthesis, Chemistry, Planar, Yield (engineering), Catalysis, Context (archaeology), Combinatorial chemistry, Kinetic energy, Phenols, Organic chemistry, Computational chemistry, Materials science, Computer science, Physics, Biology, Quantum mechanics, Computer graphics (images), Metallurgy, PaleontologyTop concepts (fields/topics) attached by OpenAlex
- Cited by
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1Total citation count in OpenAlex
- Citations by year (recent)
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2025: 1Per-year citation counts (last 5 years)
- References (count)
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183Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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