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Updated: Jul 19, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Enantioselective [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones: vicinal quaternary stereocenters
1Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China plu@fudan.edu.cn.
Abstract:
Cycloaddition is a fundamental transformation, featuring the assembly of complex cyclic molecules with multiple stereocenters. We report here a silver-catalyzed [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones with an array of azomethine ylide precursors iminoesters, furnishing azabicycles in good yields and enantioselectivities. Up to three contiguous all-carbon quaternary centers, including two angular stereocenters, could be constructed efficiently, due to high reactivity of strained cyclobutenones. Subsequent skeletal remodeling provided versatile molecules with distinct structural characters.
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