Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 3, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103789
Keywords
cyclisation; cyclopentanamine; cyclopentanol; Weinreb amide; zirconium hydride
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Funding
- University of Reims Champagne Ardenne
- CNRS
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The diastereoselective access to cyclopentanols and N,O-dimethylcyclopentylhydroxylamines from 4-pentenoic acid-derived Weinreb amides is described in this study, demonstrating a significant potential for future research.
The diastereoselective access to cyclopentanols and N,O-dimethylcyclopentylhydroxylamines from 4-pentenoic acid-derived Weinreb amides is described. Based on the concomitant generation of both the nucleophilic and the electrophilic poles by hydrozirconation of the amide and the C=C double bond, the cyclisation may be tuned towards cyclopentanols or N,O-dimethylcyclopentylhydroxylamines depending on the ring-closure promotor. An extension to cis 3-substituted N,O-dimethylcyclohexylhydroxylamines is also presented.
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