An unprecedented intermolecular [4 + 2] cycloaddition of benzocyclobutylamines with α-substituted vinylketones enabled by photoredox catalysis has been developed. The current method enables a facile access to highly functionalized cyclohexylamine derivatives that were otherwise inaccessible in moderate to good yields with excellent diastereoselectivities. This protocol owned some excellent features, such as full atom economy, good functional group compatibility, mild reaction conditions, and overall redox-neutral process. Additionally, an asymmetric version of this cycloaddition was primarily investigated by the incorporation of a chiral CPA, and moderate to good enantioselectivity could be well realized with exclusive diastereoselectivity. Synthetic applications were demonstrated by scale-up experiment and elaborations to access amino alcohol and cyclobutene derivatives. Based on the results of control experiments, a reasonable reaction mechanism was proposed to elucidate the reaction pathway.

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