Breaking the C-3-symmetry of chiral tripodal oxazolines: Enantio-discrimination of chiral organoammonium ions
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SCOPUS
- Title
- Breaking the C-3-symmetry of chiral tripodal oxazolines: Enantio-discrimination of chiral organoammonium ions
- Authors
- Kim, J; Kim, SG; Seong, HR; Ahn, KH
- Date Issued
- 2005-09-02
- Publisher
- AMER CHEMICAL SOC
- Abstract
- A phenylglycinol-derived tripodal oxazoline with C-1-symmetry (C-1-PhBTO) was synthesized, and its enantioselective recognition behavior toward alpha-chiral primary organoammonium ions was studied. The C-1-PhBTO receptor showed higher selectivity with an opposite sense of enantio-discrimination compared to other C-1-symmetric analogues examined but lower selectivity with the same sense of enantioselection compared to its C-3-symmetric analogue. Binding studies indicated that the Cl-symmetric receptors, particularly C-1-PhBTO, interact with the guests in a 2:1 host-guest complex mode in stark contrast to its C3-symmetric analogues.
- Keywords
- HOST-GUEST COMPLEXATION; AMINO-ACID DERIVATIVES; ENANTIOSELECTIVE COMPLEXATION; MOLECULAR RECOGNITION; RECEPTORS; SALTS; TRANSPORT
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/24416
- DOI
- 10.1021/JO050872P
- ISSN
- 0022-3263
- Article Type
- Article
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, vol. 70, no. 18, page. 7227 - 7231, 2005-09-02
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