Palladium-Mediated Annulation of Vinyl Aziridines with Michael Acceptors: Stereocontrolled Synthesis of Substituted Pyrrolidines and Its Application in a Formal Synthesis of (−)-α-Kainic Acid

Palladium-Mediated Annulation of Vinyl Aziridines with Michael Acceptors: Stereocontrolled Synthesis of Substituted Pyrrolidines and Its Application in a Formal Synthesis of (−)-α-Kainic Acid

Just add salt: Vinyl aziridines have been treated with methyl vinyl ketone or ethyl thioacrylate in the presence of Pd0 to give pyrrolidines with moderate to good diastereoselectivity. The presence of nBu4NCl was critical to successful annulation. The synthetic utility of the methodology has been de...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-07, Vol.50 (28), p.6370-6374
Hauptverfasser: Lowe, Martin A., Ostovar, Mehrnoosh, Ferrini, Serena, Chen, C. Chun, Lawrence, Paul G., Fontana, Francesco, Calabrese, Andrew A., Aggarwal, Varinder K.
Format: Artikel
Sprache:eng
Schlagworte:
annulation
aziridines
Aziridines - chemistry
Butanones - chemistry
Catalysis
Cyclization
Kainic Acid - chemical synthesis
Kainic Acid - chemistry
palladium
Palladium - chemistry
pyrrolidines
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Stereoisomerism
synthetic methods
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Beschreibung
Zusammenfassung:Just add salt: Vinyl aziridines have been treated with methyl vinyl ketone or ethyl thioacrylate in the presence of Pd0 to give pyrrolidines with moderate to good diastereoselectivity. The presence of nBu4NCl was critical to successful annulation. The synthetic utility of the methodology has been demonstrated in a short (formal) synthesis of (−)‐α‐kainic acid.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201101389