Dithioallyl cation (3+2) cycloadditions under aprotic reaction conditions : rapid access to spiro-fused cyclopentane scaffolds
- Author
- Frederick Degroote (UGent) , Bram Denoo, Bram Ryckaert (UGent) , Brenda Callebaut, Kristof Van Hecke (UGent) , Jan Hullaert and Johan Winne (UGent)
- Organization
- Project
-
- Sulfone derivatives - a new chemistry platform for the next generation of dynamic covalent materials
- Dearomative cycloadditions: finding novel reactivity in well-known chemical space
- Tailored crystals on-demand: gaining a full understanding of the crystallization of low-dimsional hybrid perovskites.
- Sustainable chemistry for the synthesis of fine chemicals
- Donor-acceptor carboannulations for 3D-decoration of bioactive scaffolds
- Novel heterocyclic building blocks for highly functionalized cyclopentanoid scaffolds
- Modular Synthesis Strategies for Screening Collections of Unnatural Kaurane-Type Alkaloids.
- Modulaire syntheseroutes voor de pluripotente guaianolide-scaffold
- Abstract
- We report a general method to effect all-carbon (3 + 2) cycloadditions that can elaborate cyclopentenes from a range of olefins. The required dithioallyl cation reagents can be generated in a newly developed mild protocol starting from 2-allyloxypyridine precursors, thus avoiding the use of strong Brønsted acids. The novel method significantly expands the substrate scope, which now also includes acid-sensitive olefins, and thus enables the preparation of previously inaccessible spiro-fused scaffold types from simple and readily available starting materials.
- Keywords
- CONSTRUCTION, ANNULATION, IONS
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01HRW2MZ4J7JTF2YB5NNFP593G
- MLA
- Degroote, Frederick, et al. “Dithioallyl Cation (3+2) Cycloadditions under Aprotic Reaction Conditions : Rapid Access to Spiro-Fused Cyclopentane Scaffolds.” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 21, no. 40, 2023, pp. 8117–24, doi:10.1039/d3ob01273e.
- APA
- Degroote, F., Denoo, B., Ryckaert, B., Callebaut, B., Van Hecke, K., Hullaert, J., & Winne, J. (2023). Dithioallyl cation (3+2) cycloadditions under aprotic reaction conditions : rapid access to spiro-fused cyclopentane scaffolds. ORGANIC & BIOMOLECULAR CHEMISTRY, 21(40), 8117–8124. https://doi.org/10.1039/d3ob01273e
- Chicago author-date
- Degroote, Frederick, Bram Denoo, Bram Ryckaert, Brenda Callebaut, Kristof Van Hecke, Jan Hullaert, and Johan Winne. 2023. “Dithioallyl Cation (3+2) Cycloadditions under Aprotic Reaction Conditions : Rapid Access to Spiro-Fused Cyclopentane Scaffolds.” ORGANIC & BIOMOLECULAR CHEMISTRY 21 (40): 8117–24. https://doi.org/10.1039/d3ob01273e.
- Chicago author-date (all authors)
- Degroote, Frederick, Bram Denoo, Bram Ryckaert, Brenda Callebaut, Kristof Van Hecke, Jan Hullaert, and Johan Winne. 2023. “Dithioallyl Cation (3+2) Cycloadditions under Aprotic Reaction Conditions : Rapid Access to Spiro-Fused Cyclopentane Scaffolds.” ORGANIC & BIOMOLECULAR CHEMISTRY 21 (40): 8117–8124. doi:10.1039/d3ob01273e.
- Vancouver
- 1.Degroote F, Denoo B, Ryckaert B, Callebaut B, Van Hecke K, Hullaert J, et al. Dithioallyl cation (3+2) cycloadditions under aprotic reaction conditions : rapid access to spiro-fused cyclopentane scaffolds. ORGANIC & BIOMOLECULAR CHEMISTRY. 2023;21(40):8117–24.
- IEEE
- [1]F. Degroote et al., “Dithioallyl cation (3+2) cycloadditions under aprotic reaction conditions : rapid access to spiro-fused cyclopentane scaffolds,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 21, no. 40, pp. 8117–8124, 2023.
@article{01HRW2MZ4J7JTF2YB5NNFP593G,
abstract = {{We report a general method to effect all-carbon (3 + 2) cycloadditions that can elaborate cyclopentenes from a range of olefins. The required dithioallyl cation reagents can be generated in a newly developed mild protocol starting from 2-allyloxypyridine precursors, thus avoiding the use of strong Brønsted acids. The novel method significantly expands the substrate scope, which now also includes acid-sensitive olefins, and thus enables the preparation of previously inaccessible spiro-fused scaffold types from simple and readily available starting materials.}},
author = {{Degroote, Frederick and Denoo, Bram and Ryckaert, Bram and Callebaut, Brenda and Van Hecke, Kristof and Hullaert, Jan and Winne, Johan}},
issn = {{1477-0520}},
journal = {{ORGANIC & BIOMOLECULAR CHEMISTRY}},
keywords = {{CONSTRUCTION,ANNULATION,IONS}},
language = {{eng}},
number = {{40}},
pages = {{8117--8124}},
title = {{Dithioallyl cation (3+2) cycloadditions under aprotic reaction conditions : rapid access to spiro-fused cyclopentane scaffolds}},
url = {{http://doi.org/10.1039/d3ob01273e}},
volume = {{21}},
year = {{2023}},
}
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