Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 11, Pages 7714-7724Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00676
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Funding
- National Natural Science Foundation of China [21801061]
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This unprecedented 1,3-dipole cycloaddition between acyclic CF3-ketimines and N-benzyl azomethine ylide has been enabled by tungsten catalysis, leading to a range of novel imidazolidines with a trifluoromethylated tetrasubstituted carbon center. The gram-scale synthesis capability and variant derivatizations of cycloaddition adducts demonstrate the synthetic potential of this approach, providing easy access to a rapidly expanding library of motifs with a trifluoromethylated fully substituted carbon.
An unprecedented 1,3-dipole cycloaddition between acyclic CF3-ketimines and N-benzyl azomethine ylide has been allowed by tungsten catalysis, furnishing a range of novel imidazolidines bearing a trifluoromethylated tetrasubstituted carbon center. This reaction appears as one of rare examples that challenging acyclic CF3-ketimines have been engaged in 1,3-cycloaddition reactions. The capability for gram-scale synthesis and variant derivatizations of cycloaddition adducts illustrates the synthetic potential of this approach. This protocol provides a facile access to a rapidly enlarging pool of motifs with a trifluoromethylated fully substituted carbon.
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