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- Title
Rhodium(I)-Catalyzed Bridged [5+2] Cycloaddition of cis-Allene-vinylcyclopropanes to Synthesize the Bicyclo[4.3.1]decane Skeleton.
- Authors
Liu, Cheng‐Hang; Yu, Zhi‐Xiang
- Abstract
Previously reported was that cis-ene-vinylcyclopropanes (cis-ene-VCPs) underwent Rh-catalyzed [5+2] reaction to give 5,7-fused bicyclic products, where vinylcyclopropane (VCP) acts as five-carbon synthon. Unfortunately, this reaction had very limited scope. Replacing the 2π component of cis-ene-VCPs to allene moiety, the corresponding cis-allene-VCPs did not undergo the expected normal [5+2] cycloaddition to give 5,7-fused bicyclic products. Instead, the challenging bicyclo[4.3.1]decane skeleton was obtained via an unprecedented bridged [5+2] cycloaddition. DFT calculations were applied to understand why this bridged [5+2] reaction is favored over the anticipated but not realized normal [5+2] reaction.
- Subjects
RHODIUM catalysts; RING formation (Chemistry); VINYLCYCLOPROPANES; BICYCLODECENES; DENSITY functional theory
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 30, p8793
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201702288