Journal
RSC ADVANCES
Volume 5, Issue 32, Pages 24824-24833Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ra15284k
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Funding
- National Natural Science Foundation of China [21202153]
- Foundation of Zhejiang Educational Committee [Y201223263]
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A possible mechanism of dynamic kinetic resolution by the formation of N-tert-butoxycarbonylthiazolidine carboxylic acid was proposed and validated by a quantitative density functional theoretical calculation according to Curtin-Hammett principle. Such a mechanism of action of a nucleophilic substitution reaction through an intramolecular hydrogen bonding could be widely applied in the organic syntheses of particular enantiomer. Antibacterial activities showed that most of the N-tert-butoxycarbonyl-(2R)-arylthiazolidine-(4R)-carboxylic acid derivatives exhibited better antibacterial activities against the four bacterial strains than related (2RS)-arylthiazolidine-(4R)-carboxylic acid derivatives.
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