Optically Active Bicyclic N-Heterocycles by Organocatalytic Asymmetric Michael Addition/Cyclization Sequences

Optically Active Bicyclic N-Heterocycles by Organocatalytic Asymmetric Michael Addition/Cyclization Sequences

Highly stereoselective one‐pot syntheses of various optically active N‐heterocyclic bicycles have been developed. The protocols are based on an organocatalytic, asymmetric Michael addition followed by a condensation/cycloaddition sequence to furnish aziridine carbonyls, β‐lactams, or octahydrobenzo[...

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Veröffentlicht in:Chemistry : a European journal 2011-04, Vol.17 (15), p.4076-4080
Hauptverfasser: Worgull, Dennis, Dickmeiss, Gustav, Jensen, Kim L., Franke, Patrick T., Holub, Nicole, Jørgensen, Karl Anker
Format: Artikel
Sprache:eng
Schlagworte:
1,3‐dipolar cycloaddition
3-dipolar cycloaddition
Chemistry
N-heterocycles
one-pot reactions
organocatalysis
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Zusammenfassung:Highly stereoselective one‐pot syntheses of various optically active N‐heterocyclic bicycles have been developed. The protocols are based on an organocatalytic, asymmetric Michael addition followed by a condensation/cycloaddition sequence to furnish aziridine carbonyls, β‐lactams, or octahydrobenzo[c]isoxazoles depending on the reaction conditions and applied nucleophiles.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201100233