Journal
ORGANIC LETTERS
Volume 23, Issue 9, Pages 3343-3348Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00837
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Funding
- Alexander von Humboldt Foundation for the Research Group Linkage Program
- (Albert-Ludwigs-Universitat Freiburg)
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This novel copper-catalyzed cycloisomerization reaction provides a practical and efficient method for the synthesis of hexahydropyrrolo[3,4-b]azepin-5(4H)-ones by simultaneously forming four new bonds in a single step.
A novel copper-catalyzed cycloisomerization of unactivated allene-tethered O-propargyl oximes has been developed for the synthesis of hexahydropyrrolo[3,4-b]azepin-5(4H)-ones. This one-pot domino reaction proceeds via a [2,3]-sigmatropic rearrangement, a [3 + 2] cycloaddition, and another [3,3]-sigmatropic rearrangement. The methodology offers a practical and straightforward route for the rapid assembly of both ring components of the fused bicyclic motifs from acyclic precursors by simultaneously forming four new bonds (a C=O, a C=N, and two C-C bonds) in a single step.
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