An Atom-Economic Synthesis of Bicyclo[3.1.0]hexanes by Rhodium N-Heterocyclic Carbene-Catalyzed Diastereoselective Tandem Hetero-[5+2] Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, PR China.
Journal of the American Chemical Society (Impact Factor: 11.44). 05/2011; 133(19):7304-7. DOI: 10.1021/ja2014604
Source: PubMed

ABSTRACT The first synthetic application of a vinylic oxirane as a heteroatom-containing five-atom component in transition-metal-catalyzed cycloaddition reactions is reported. A new, efficient, diastereoselective tandem intramolecular hetero-[5+2] cycloaddition/Claisen rearrangement of vinylic oxirane-alkyne substrates that uses a rhodium NHC complex and provides strategically novel, atom-economic, regiospecific, and diastereoselective access to [3.1.0] bicyclic products has been developed.

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