4.5 Article

Energy Transfer Catalysis by Visible Light: Atrop- and Regio-Selective Intermolecular [2+2]-Photocycloaddition of Maleimide with Alkenes

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 10, Pages 1478-1481

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901157

Keywords

Atropselective photoreactions; Photochirogenesis; Asymmetric photochemistry; Chiral photochemistry; Energy transfer catalysis

Funding

  1. National Science Foundation [CHE-1811795]
  2. BGSU
  3. center for photochemical Sciences

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Intermolecular [2+2]-photocycloaddition of atropisomeric phenyl maleimide has been evaluated with substituted alkenes with complete control over regiochemistry. We were also successful in carrying out atropselective reactions with the removal of axial chirality leading to enantio-enriched photoproducts. Based on detailed photophysical studies, a mechanistic rationale is proposed for the observed selectivity.

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