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- Title
Enantioselective Synthesis of Cyclic Nitrones by Chemoselective Intramolecular Allylic Alkylation of Oximes.
- Authors
Sandmeier, Tobias; Carreira, Erick M.
- Abstract
The enantio‐ and chemoselective iridium‐catalyzed N‐allylation of oximes is described for the first time. Intramolecular kinetic resolution provides access to cyclic nitrones and enantioenriched aliphatic allylic alcohols. Salient features of this transformation are its ability to employ E/Z‐isomeric mixtures of oxime starting materials convergently and high functional group tolerance. The implementation of N‐allylation/1,3‐dipolar cycloaddition reaction sequences furnishes tricyclic isoxazolidines in highly enantio‐ and diastereoselective fashion. The synthetic utility of the approach is demonstrated by the efficient, formal synthesis of the marine natural product (+)‐halichlorine.
- Subjects
ALLYLIC alkylation; NITRONES; OXIMES; MARINE natural products; ALIPHATIC alcohols; ALLYL alcohol; KINETIC resolution
- Publication
Angewandte Chemie, 2021, Vol 133, Issue 18, p10001
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202100150