A copper-catalyzed atom economical O-transfer reaction strategy was developed for the synthesis of densely functionalized γ-lactones from N-vinyl-α,β-unsaturated nitrones and ketenes.
A variety of N-vinylindoles and N-vinylpyrroles were prepared in moderate to good yields through the nickel(II)catalyzed [3 + 2] cycloaddition of α,β-unsaturated nitrones with allenoates under mild reaction conditions. A rational mechanism for the formation of N-vinylindoles was proposed based on the 18 O-labeled experiments and key intermediates detected by highresolution mass spectrometry trace experiments. The present method highlights a nickel(II)-controlled cyclization, atomeconomical reaction, broad substrate scope, good functional group tolerance, and high Z-stereoselectivity for the enamine bond.
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