Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 14, Pages 6449-6455Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b13080
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Funding
- National Science Foundation [CHE-1665008, CHE-1726291, CHE-1828183]
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Arene cyclopropanation offers a direct route to higher-order, non-aromatic carbocycles; however, the inherent issue of dictating site selectivity has cumbered the development of novel intermolecular reactions that directly engage the arene pool. This paper describes a highly regio- and stereoselective, Rh-2[(S)-PTTL](4)-catalyzed arene cyclopropanation using alpha-cyanodiazoacetates to afford stable norcaradienes bearing three stereogenic centers, one of which is an all-carbon quaternary center. The enantioenriched norcaradienes served as tunable templates for further transformation into stereochemically dense, fused and bicyclic carbocycles containing transmutable functionality.
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