Abstract
TRANSFER of chirality and multiplication of chiral molecules are key processes in the chemical and biochemical transformations of natural and synthetic compounds. For entropic reasons, structural immobilization in enzymatic and catalytic processes and the use of low temperatures should generally enhance the optical yield (preference for one enantiomer) in chiral reactions. Studies of the temperature dependence of optical yield in chemical and biochemical processes have, however, been sporadic1–10. Here we report a systematic study of the temperature dependence of the photosensitized enantiodifferentiating isomerization of a simple alkene. We find that above a critical temperature, characteristic of the photosensitizer used, the optical yield increases with increasing temperature, apparently conflicting with the widely accepted view that lower temperatures favour a higher optical yield. Thus both enantiomers may be produced with high efficiency using a single chiral source. This implies that transfer and multiplication of chirality in natural systems, an important aspect of the development of prebiotic organic molecules, may be effected rather more simply than has hitherto been supposed.
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Inoue, Y., Yokoyama, T., Yamasaki, N. et al. An optical yield that increases with temperature in a photochemically induced enantiomeric isomerization. Nature 341, 225–226 (1989). https://doi.org/10.1038/341225a0
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DOI: https://doi.org/10.1038/341225a0
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