Journal
ORGANIC LETTERS
Volume 24, Issue 1, Pages 137-141Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03746
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- Bristol Chemical Synthesis Centre for Doctoral Training, EPSRC [EP/G036764/1]
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This study demonstrates a method for the synthesis of densely functionalized cyclobutanes with high regio- and diastereoselectivity, utilizing a sequential photocatalysis strategy to rapidly assemble structurally complex 3-azabicyclo[3.2.0] heptane scaffolds. The installation of all-carbon quaternary stereocenters is achieved through triplet sensitized [2 + 2] photocycloadditions followed by photoredox-catalyzed dechlorinative C-C bond forming reactions.
The synthesis of densely functionalized cyclobutanes containing all-carbon quaternary stereocenters in high regio- and diastereoselectivity remains synthetically challenging. Herein, we show that this can be achieved by using a sequential photocatalysis strategy, wherein 3-chloromaleimides undergo triplet sensitized [2 + 2] photocycloadditions with alkynes or alkenes followed by photoredox-catalyzed dechlorinative C-C bond forming reactions to install quaternary stereocenters. This allows the rapid assembly of structurally complex and sterically congested 3-azabicyclo[3.2.0] heptane scaffolds from readily available starting materials.
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