Photoswitchable Chiral Phase Transfer Catalyst
Masaru Kondo, Kento Nakamura, Chandu G. Krishnan, Shinobu Takizawa, Tsukasa Abe, Hiroaki Sasai
Abstract
Azo-crown ether-based photoswitching chiral phase transfer catalysts have been developed to control the catalytic activity by photoirradiation. Azobenzene binaphthyl crown ether (ABCE) can switch its reactivity and selectivity through structural transformation of the crown ether moiety induced by E/Z photoisomerization of azobenzene. (Z)-ABCE promoted enantioselective alkylation of the glycine Schiff base to afford chiral amino acid derivatives in good yields with high enantiomer ratios. In contrast, (E)-ABCE hindered the reaction progress under the same conditions.
Topics & Concepts
AzobenzeneCrown etherPhotoisomerizationChemistryMoietyCatalysisAlkylationEnantioselective synthesisSelectivityReactivity (psychology)EtherSchiff baseCombinatorial chemistryOrganic chemistryStereochemistryIsomerizationMoleculePathologyMedicineIonAlternative medicinePhotochromic and Fluorescence ChemistryPhotoreceptor and optogenetics researchPorphyrin and Phthalocyanine Chemistry