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Enantioselective Complexation of Chiral Propylene Oxide by an Enantiopure Water-Soluble Cryptophane

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journal contribution
posted on 2011-05-20, 00:00 authored by Aude Bouchet, Thierry Brotin, Mathieu Linares, Hans Ågren, Dominique Cavagnat, Thierry Buffeteau
ECD and NMR experiments show that the complexation of propylene oxide (PrO) within the cavity of an enantiopure water-soluble cryptophane 1 in NaOH solution is enantioselective and that the (R)-PrO@PP-1 diastereomer is more stable than the (S)-PrO@PP-1 diastereomer with a free energy difference of 1.7 kJ/mol. This result has been confirmed by molecular dynamics (MD) and ab initio calculations. The enantioselectivity is preserved in LiOH and KOH solutions even though the binding constants decrease, whereas PrO is not complexed in CsOH solution.

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