Confronting the Challenging Asymmetric Carbonyl 1,2-Addition Using Vinyl Heteroarene Pronucleophiles: Ligand-Controlled Regiodivergent Processes through a Dearomatized Allyl–Cu Species Article Swipe
Yuyang Dong
,
Alexander W. Schuppe
,
Binh Khanh
,
Peng Liu
,
Stephen L. Buchwald
·
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.1021/jacs.2c00734
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.1021/jacs.2c00734
The selective reductive coupling of vinyl heteroarenes with aldehydes and ketones represents a versatile approach for the rapid construction of enantiomerically enriched secondary and tertiary alcohols, respectively. Herein, we demonstrate a CuH-catalyzed regiodivergent coupling of vinyl heteroarenes with carbonyl-containing electrophiles, in which the selectivity is controlled by the ancillary ligand. This approach leverages an in situ generated benzyl- or dearomatized allyl-Cu intermediate, yielding either the dearomatized or exocyclic addition products, respectively. The method exhibits excellent regio-, diastereo-, and enantioselectivity and tolerates a range of common functional groups and heterocycles. The dearomative pathway allows direct access to a variety of functionalized saturated heterocyclic structures. The reaction mechanism was probed using a combination of experimental and computational approach. Density functional theory studies suggest that the ligand-controlled regioselectivity results from the C-H/π interaction and steric repulsion in transition states, leading to the major and minor regioisomers, respectively. Hydrocupration of vinyl heteroarene pronucleophile is the enantiodetermining step, whereas the diastereoselectivity is enforced by steric interactions between the benzylic or allyl-Cu intermediate and carbonyl-containing substrates in a six-membered cyclic transition state.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/jacs.2c00734
- OA Status
- green
- Cited By
- 50
- References
- 75
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4220704665
All OpenAlex metadata
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https://openalex.org/W4220704665Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1021/jacs.2c00734Digital Object Identifier
- Title
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Confronting the Challenging Asymmetric Carbonyl 1,2-Addition Using Vinyl Heteroarene Pronucleophiles: Ligand-Controlled Regiodivergent Processes through a Dearomatized Allyl–Cu SpeciesWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2022Year of publication
- Publication date
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2022-03-26Full publication date if available
- Authors
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Yuyang Dong, Alexander W. Schuppe, Binh Khanh, Peng Liu, Stephen L. BuchwaldList of authors in order
- Landing page
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https://doi.org/10.1021/jacs.2c00734Publisher landing page
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YesWhether a free full text is available
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greenOpen access status per OpenAlex
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https://www.ncbi.nlm.nih.gov/pmc/articles/9202959Direct OA link when available
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Chemistry, Regioselectivity, Steric effects, Electrophile, Ligand (biochemistry), Selectivity, Combinatorial chemistry, Structural isomer, Organic chemistry, Medicinal chemistry, Stereochemistry, Catalysis, Receptor, BiochemistryTop concepts (fields/topics) attached by OpenAlex
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50Total citation count in OpenAlex
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2025: 8, 2024: 12, 2023: 20, 2022: 10Per-year citation counts (last 5 years)
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10Other works algorithmically related by OpenAlex
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