- Author
- Bram Ryckaert (UGent) , Jan Hullaert, Kristof Van Hecke (UGent) and Johan Winne (UGent)
- Organization
- Project
-
- 3D Structureel Platform voor Chemische Excellentie .
- Study of nucleation and crystal growth of pharmaceuticals by X-ray and harmonic light scattering
- Novel heterocyclic building blocks for highly functionalized cyclopentanoid scaffolds
- Dearomative cycloadditions: finding novel reactivity in well-known chemical space
- Abstract
- The (3 + 2) cycloaddition of various indoles with a dithioallyl cation affords dearomatized cyclopentannulated adducts, with complete control of regioselectivity and excellent chemo- and diastereoselectivity. The success of the reaction critically relies on the use of an excess of very strong Bronsted acid, which paradoxically prevents carbocationic side reactions. The reaction tolerates sensitive functionalities such as basic amines or free hydroxyls, and we demonstrate its use in late stage derivatization of highly functionalized, unprotected indoles.
- Keywords
- ALLYL CATIONS, CYCLOPENTANOID, CYCLOADDITION
Downloads
-
(...).pdf
- full text (Published version)
- |
- UGent only
- |
- |
- 1.05 MB
-
Ryckaert AAM OL 2022.pdf
- full text (Accepted manuscript)
- |
- open access
- |
- |
- 654.59 KB
Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8764910
- MLA
- Ryckaert, Bram, et al. “Dearomative (3+2) Cycloadditions of Unprotected Indoles.” ORGANIC LETTERS, vol. 24, no. 23, 2022, pp. 4119–23, doi:10.1021/acs.orglett.2c01214.
- APA
- Ryckaert, B., Hullaert, J., Van Hecke, K., & Winne, J. (2022). Dearomative (3+2) cycloadditions of unprotected indoles. ORGANIC LETTERS, 24(23), 4119–4123. https://doi.org/10.1021/acs.orglett.2c01214
- Chicago author-date
- Ryckaert, Bram, Jan Hullaert, Kristof Van Hecke, and Johan Winne. 2022. “Dearomative (3+2) Cycloadditions of Unprotected Indoles.” ORGANIC LETTERS 24 (23): 4119–23. https://doi.org/10.1021/acs.orglett.2c01214.
- Chicago author-date (all authors)
- Ryckaert, Bram, Jan Hullaert, Kristof Van Hecke, and Johan Winne. 2022. “Dearomative (3+2) Cycloadditions of Unprotected Indoles.” ORGANIC LETTERS 24 (23): 4119–4123. doi:10.1021/acs.orglett.2c01214.
- Vancouver
- 1.Ryckaert B, Hullaert J, Van Hecke K, Winne J. Dearomative (3+2) cycloadditions of unprotected indoles. ORGANIC LETTERS. 2022;24(23):4119–23.
- IEEE
- [1]B. Ryckaert, J. Hullaert, K. Van Hecke, and J. Winne, “Dearomative (3+2) cycloadditions of unprotected indoles,” ORGANIC LETTERS, vol. 24, no. 23, pp. 4119–4123, 2022.
@article{8764910,
abstract = {{The (3 + 2) cycloaddition of various indoles with a dithioallyl cation affords dearomatized cyclopentannulated adducts, with complete control of regioselectivity and excellent chemo- and diastereoselectivity. The success of the reaction critically relies on the use of an excess of very strong Bronsted acid, which paradoxically prevents carbocationic side reactions. The reaction tolerates sensitive functionalities such as basic amines or free hydroxyls, and we demonstrate its use in late stage derivatization of highly functionalized, unprotected indoles.}},
author = {{Ryckaert, Bram and Hullaert, Jan and Van Hecke, Kristof and Winne, Johan}},
issn = {{1523-7060}},
journal = {{ORGANIC LETTERS}},
keywords = {{ALLYL CATIONS,CYCLOPENTANOID,CYCLOADDITION}},
language = {{eng}},
number = {{23}},
pages = {{4119--4123}},
title = {{Dearomative (3+2) cycloadditions of unprotected indoles}},
url = {{http://doi.org/10.1021/acs.orglett.2c01214}},
volume = {{24}},
year = {{2022}},
}
- Altmetric
- View in Altmetric
- Web of Science
- Times cited: