16141-45-0Relevant academic research and scientific papers
Enantioselective Visible-Light-Mediated Formation of 3-Cyclopropylquinolones by Triplet-Sensitized Deracemization
Tr?ster, Andreas,Bauer, Andreas,Jandl, Christian,Bach, Thorsten
, p. 3538 - 3541 (2019)
3-Allyl-substituted quinolones undergo a triplet-sensitized di-π-methane rearrangement reaction to the corresponding 3-cyclopropylquinolones upon irradiation with visible light (λ=420 nm). A chiral hydrogen-bonding sensitizer (10 mol %) was shown to promote the reaction enantioselectively (88–96 % yield, 32–55 % ee). Surprisingly, it was found that the enantiodifferentiation does not occur at the state of initial product formation but that it is the result of a deracemization event. The individual parameters that control the distribution of enantiomers in the photostationary state have been identified.
