Organocatalytic Asymmetric Desymmetrization-Fragmentation of Cyclic Ketones

Organocatalytic Asymmetric Desymmetrization-Fragmentation of Cyclic Ketones

A ticket to total synthesis: The title reaction of meso cyclopropane cyclopentanones and epoxycyclopentanones was catalyzed by thiourea‐containing cinchona alkaloids with good to excellent enantioselectivity (see scheme). The concept was extended to a one‐pot asymmetric desymmetrization–fragmentatio...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (36), p.6650-6653
Hauptverfasser: Dickmeiss, Gustav, De Sio, Vincenzo, Udmark, Jonas, Poulsen, Thomas B, Marcos, Vanesa, Jørgensen, Karl Anker
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric catalysis
cinchona alkaloids
desymmetrization
fragmentation
thiourea functionality
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Beschreibung
Zusammenfassung:A ticket to total synthesis: The title reaction of meso cyclopropane cyclopentanones and epoxycyclopentanones was catalyzed by thiourea‐containing cinchona alkaloids with good to excellent enantioselectivity (see scheme). The concept was extended to a one‐pot asymmetric desymmetrization–fragmentation–Michael addition by including a nucleophile. A kinetic resolution based on this method was also demonstrated.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200903253