Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes

Enantioselective Palladium-Catalyzed [3C + 2C] and [4C + 3C] Intramolecular Cycloadditions of Alkylidenecyclopropanes

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, phosphoramidit...

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Veröffentlicht in:ACS catalysis 2018-07, Vol.8 (7), p.6100-6105
Hauptverfasser: Verdugo, Felipe, Villarino, Lara, Durán, Juan, Gulías, Moisés, Mascareñas, José L, López, Fernando
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container_end_page 6105
container_issue 7
container_start_page 6100
container_title ACS catalysis
container_volume 8
creator Verdugo, Felipe
Villarino, Lara
Durán, Juan
Gulías, Moisés
Mascareñas, José L
López, Fernando
description 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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