Enantioselective [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones: vicinal quaternary stereocenters construction and skeletal functionalization.

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.

SUBMITTER: Lu L 

PROVIDER: S-EPMC10411620 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature