(5,6-Dihydro-1,4-dithiin-2-yl)methanol as a versatile allyl-cation equivalent in (3+2) cycloaddition reactions
- Author
- Jan Hullaert and Johan Winne (UGent)
- Organization
- Abstract
- The title heterocyclic alcohol readily generates a sulfur-substituted allylic cation upon simple treatment with a protic acid, thus facilitating a synthetically useful stepwise (3+2) cycloaddition reaction pathway with a range of conjugated-olefin-type substrates. The introduction of an allyl fragment in this way provided rapid access to a variety of cyclopentanoid scaffolds. The cyclic nature of the cation precursor alcohol was shown to be instrumental for efficient cycloaddition reactions to take place, thus indicating an attractive strategy for controlling the reactivity of heteroatom-substituted allyl cations. The formal cycloaddition reaction is highly regio- and stereoselective and was also used for a short total synthesis of the natural product cuparene in racemic form through a cycloaddition–hydrodesulfurization sequence.
- Keywords
- fused-ring systems, thionium ions, cyclopentanoids, allyl cations, cycloaddition, INTRAMOLECULAR 4+3 CYCLOADDITIONS, BIOSYNTHESIS SPECULATION, EFFICIENT SYNTHESES, VINYLTHIONIUM IONS, (+/-)-CUPARENE, ANNULATION, CONSTRUCTION, CYCLIZATION, PYRROLOINDOLINES, PLUMARELLIDE
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8107662
- MLA
- Hullaert, Jan, and Johan Winne. “(5,6-Dihydro-1,4-Dithiin-2-Yl)Methanol as a Versatile Allyl-Cation Equivalent in (3+2) Cycloaddition Reactions.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 55, no. 42, 2016, pp. 13254–58, doi:10.1002/anie.201606411.
- APA
- Hullaert, J., & Winne, J. (2016). (5,6-Dihydro-1,4-dithiin-2-yl)methanol as a versatile allyl-cation equivalent in (3+2) cycloaddition reactions. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 55(42), 13254–13258. https://doi.org/10.1002/anie.201606411
- Chicago author-date
- Hullaert, Jan, and Johan Winne. 2016. “(5,6-Dihydro-1,4-Dithiin-2-Yl)Methanol as a Versatile Allyl-Cation Equivalent in (3+2) Cycloaddition Reactions.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55 (42): 13254–58. https://doi.org/10.1002/anie.201606411.
- Chicago author-date (all authors)
- Hullaert, Jan, and Johan Winne. 2016. “(5,6-Dihydro-1,4-Dithiin-2-Yl)Methanol as a Versatile Allyl-Cation Equivalent in (3+2) Cycloaddition Reactions.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55 (42): 13254–13258. doi:10.1002/anie.201606411.
- Vancouver
- 1.Hullaert J, Winne J. (5,6-Dihydro-1,4-dithiin-2-yl)methanol as a versatile allyl-cation equivalent in (3+2) cycloaddition reactions. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2016;55(42):13254–8.
- IEEE
- [1]J. Hullaert and J. Winne, “(5,6-Dihydro-1,4-dithiin-2-yl)methanol as a versatile allyl-cation equivalent in (3+2) cycloaddition reactions,” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 55, no. 42, pp. 13254–13258, 2016.
@article{8107662,
abstract = {{The title heterocyclic alcohol readily generates a sulfur-substituted allylic cation upon simple treatment with a protic acid, thus facilitating a synthetically useful stepwise (3+2) cycloaddition reaction pathway with a range of conjugated-olefin-type substrates. The introduction of an allyl fragment in this way provided rapid access to a variety of cyclopentanoid scaffolds. The cyclic nature of the cation precursor alcohol was shown to be instrumental for efficient cycloaddition reactions to take place, thus indicating an attractive strategy for controlling the reactivity of heteroatom-substituted allyl cations. The formal cycloaddition reaction is highly regio- and stereoselective and was also used for a short total synthesis of the natural product cuparene in racemic form through a cycloaddition–hydrodesulfurization sequence.}},
author = {{Hullaert, Jan and Winne, Johan}},
issn = {{1433-7851}},
journal = {{ANGEWANDTE CHEMIE-INTERNATIONAL EDITION}},
keywords = {{fused-ring systems,thionium ions,cyclopentanoids,allyl cations,cycloaddition,INTRAMOLECULAR 4+3 CYCLOADDITIONS,BIOSYNTHESIS SPECULATION,EFFICIENT SYNTHESES,VINYLTHIONIUM IONS,(+/-)-CUPARENE,ANNULATION,CONSTRUCTION,CYCLIZATION,PYRROLOINDOLINES,PLUMARELLIDE}},
language = {{eng}},
number = {{42}},
pages = {{13254--13258}},
title = {{(5,6-Dihydro-1,4-dithiin-2-yl)methanol as a versatile allyl-cation equivalent in (3+2) cycloaddition reactions}},
url = {{http://doi.org/10.1002/anie.201606411}},
volume = {{55}},
year = {{2016}},
}
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