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Issue 7, 2015
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Dual wavelength asymmetric photochemical synthesis with circularly polarized light

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Abstract

Asymmetric photochemical synthesis using circularly polarized (CP) light is theoretically attractive as a means of absolute asymmetric synthesis and postulated as an explanation for homochirality on Earth. Using an asymmetric photochemical synthesis of a dihydrohelicene as an example, we demonstrate the principle that two wavelengths of CP light can be used to control separate reactions. In doing so, a photostationary state (PSS) is set up in such a way that the enantiomeric induction intrinsic to each step can combine additively, significantly increasing the asymmetric induction possible in these reactions. Moreover, we show that the effects of this dual wavelength approach can be accurately determined by kinetic modelling of the PSS. Finally, by coupling a PSS to a thermal reaction to trap the photoproduct, we demonstrate that higher enantioselectivity can be achieved than that obtainable with single wavelength irradiation, without compromising the yield of the final product.

Graphical abstract: Dual wavelength asymmetric photochemical synthesis with circularly polarized light

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Publication details

The article was received on 16 Dec 2014, accepted on 16 Apr 2015 and first published on 16 Apr 2015


Article type: Edge Article
DOI: 10.1039/C4SC03897E
Citation: Chem. Sci., 2015,6, 3853-3862
  • Open access: Creative Commons BY license
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    Dual wavelength asymmetric photochemical synthesis with circularly polarized light

    R. D. Richardson, M. G. J. Baud, C. E. Weston, H. S. Rzepa, M. K. Kuimova and M. J. Fuchter, Chem. Sci., 2015, 6, 3853
    DOI: 10.1039/C4SC03897E

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