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Published on: February 7, 2019
Cu/Rh-Carbene-Directed Highly Diastereoselective Dimerization of Cyclopropenes
Lijuan Ma1, Meiling Dai1, Xinyu Liu1
1Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang443002, China.
Abstract:
Carbene dimerization typically proceeds through head-to-head coupling to form planar olefins. Herein we report a carbene dimerization of cyclopropenes under copper or rhodium catalysis that proceeds through sequential C-H insertion and [2 + 1] cycloaddition to furnish cyclopropa-fused indanes with excellent diastereoselectivities. The reaction features broad substrate scope, gram-scale synthesis, and versatile product transformations. Mechanistic studies and DFT calculations reveal that π-π stacking interactions govern the high diastereoselectivity.
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