4.6 Article

Photo-auxiliary approach to control excited state reactivity: Cross [2+2]-photocycloaddition of oxazolidinone based hydrazides

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jphotochem.2019.111883

Keywords

Photochiral auxiliary; Photoreactions of hydrazides; Photocatalysis; Energy transfer catalysis; Photochirogenesis

Funding

  1. National Science Foundation [CHE-1465075, CHE-1811795]

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Chiral oxazolidinone based hydrazides undergo efficient cross [2 + 2]-photocycloaddition upon visible light illumination. Oxazolidinone functionality acted as an energy harvesting photo-auxiliary. The cross [2 + 2]-photocycloaddition proceeded efficiently from the excited state with moderate to excellent isolated yield of the photoproduct. The photo-auxiliary can be conveniently removed post-photoreaction, which highlights the versatility of this strategy.

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