Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 49, Pages 16746-16755Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201302735
Keywords
alkaloids; allylic compounds; enantioselectivity; iridium; lactams
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Funding
- Deutsche Forschungsgemeinschaft [SFB 623]
- Alexander von Humboldt-Foundation
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Enantioselective iridium-catalyzed allylic substitutions were used to prepare N-allyl hydroxamic acid derivatives that were suitable for ring-closing metathesis, giving N-methoxylactams. Reactions of these derivatives with Grignard or organolithium compounds gave hemiaminals, which could be reduced diastereoselectively via acyliminium intermediates to give cis-piperidines or cis-pyrrolidines with substituents in the 2,6- or 2,5-positions, respectively. In addition, compounds with a quaternary carbon center could be synthesized by corresponding reactions with potassium cyanide/AcOH. The procedures were applied in the syntheses of alkaloids (-)-209D and (+)-prosophylline.
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