Enantioselective Complexation of Chiral Propylene Oxide by an Enantiopure Water-Soluble Cryptophane
2011 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 76, no 10, 4178-4181 p.Article in journal (Refereed) Published
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 to 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.
Place, publisher, year, edition, pages
2011. Vol. 76, no 10, 4178-4181 p.
IdentifiersURN: urn:nbn:se:kth:diva-34213DOI: 10.1021/jo200519rISI: 000290465700068ScopusID: 2-s2.0-79956158513OAI: oai:DiVA.org:kth-34213DiVA: diva2:423483
FunderSwedish e‐Science Research Center
QC 201106152011-06-152011-05-302012-05-22Bibliographically approved