A Highly Enantioselective One-Pot Synthesis of Spirolactones by an Organocatalyzed Michael Addition/Cyclization Sequence

Spiroring in control: A novel organocatalytic Michael addition/cyclization sequence based on the bis(electrophilic) properties of vinyl selenones has been successfully employed for the synthesis of densely functionalized spirocyclic compounds (see scheme). By using a simple one‐pot procedure and mil...

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Veröffentlicht in:	Angewandte Chemie International Edition 2011-09, Vol.50 (40), p.9382-9385
Hauptverfasser:	Sternativo, Silvia, Calandriello, Antonella, Costantino, Ferdinando, Testaferri, Lorenzo, Tiecco, Marcello, Marini, Francesca
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Chemistry Techniques, Synthetic - methods Cyclization Lactones - chemical synthesis Lactones - chemistry Molecular Structure nucleophilic addition organocatalysis Selenium spiro compounds Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	Spiroring in control: A novel organocatalytic Michael addition/cyclization sequence based on the bis(electrophilic) properties of vinyl selenones has been successfully employed for the synthesis of densely functionalized spirocyclic compounds (see scheme). By using a simple one‐pot procedure and mild reaction conditions, spirocyclic compounds were synthesized in high yields and with high levels of enantioselectivity (90–98 % ee).
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201104819