ACS Catalysis, volume 8, issue 7, pages 6100-6105
Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes
2
Instituto de Química Orgánica General CSIC, Juan de la Cierva 3, 28006, Madrid, Spain
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Publication type: Journal Article
Publication date: 2018-06-04
General Chemistry
Catalysis
Abstract
We report a highly enantioselective [3C + 2C] intramolecular cycloaddition of alkylidenecyclopropanes (ACPs) and alkenes. The best results are obtained by using sterically demanding chiral phosphoramidite ligands derived from Vapol. Moreover, we also show that related, but less bulky, phosphoramidites can also lead to very effective [4C + 3C] cycloadditions when dienes, instead of alkenes, are used as reacting partners. The reactions provide a practical, simple, and selective access to optically active, synthetically appealing 5,5- and 5,7-bicyclic systems.
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Verdugo F. et al. Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes // ACS Catalysis. 2018. Vol. 8. No. 7. pp. 6100-6105.
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Verdugo F., Villarino L., Durán J., Gulías M., Mascareñas J. L., Lopez F. Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes // ACS Catalysis. 2018. Vol. 8. No. 7. pp. 6100-6105.
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TY - JOUR
DO - 10.1021/acscatal.8b01296
UR - https://doi.org/10.1021/acscatal.8b01296
TI - Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes
T2 - ACS Catalysis
AU - Verdugo, Felipe
AU - Villarino, Lara
AU - Durán, Juan
AU - Gulías, Moisés
AU - Mascareñas, José L.
AU - Lopez, Fernando
PY - 2018
DA - 2018/06/04
PB - American Chemical Society (ACS)
SP - 6100-6105
IS - 7
VL - 8
SN - 2155-5435
ER -
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@article{2018_Verdugo,
author = {Felipe Verdugo and Lara Villarino and Juan Durán and Moisés Gulías and José L. Mascareñas and Fernando Lopez},
title = {Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes},
journal = {ACS Catalysis},
year = {2018},
volume = {8},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acscatal.8b01296},
number = {7},
pages = {6100--6105},
doi = {10.1021/acscatal.8b01296}
}
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Verdugo, Felipe, et al. “Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes.” ACS Catalysis, vol. 8, no. 7, Jun. 2018, pp. 6100-6105. https://doi.org/10.1021/acscatal.8b01296.