Enantioselective Synthesis of Cyclic Nitrones by Chemoselective Intramolecular Allylic Alkylation of Oximes
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Date
2021-04-26Type
- Journal Article
Citations
Cited 16 times in
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Cited 15 times in
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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. Show more
Publication status
publishedExternal links
Journal / series
Angewandte Chemie. International EditionVolume
Pages / Article No.
Publisher
WileySubject
1,3-dipolar cycloaddition; enantioselective catalysis; iridium; nitrones; oximesOrganisational unit
03511 - Carreira, Erick M. / Carreira, Erick M.
Funding
172516 - Asymmetric Synthesis of Functionally Rich Molecules (SNF)
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Show all metadata
Citations
Cited 16 times in
Web of Science
Cited 15 times in
Scopus
ETH Bibliography
yes
Altmetrics