Photoswitchable Chiral Phase Transfer Catalyst

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/...

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Bibliographic Details
Published in:ACS catalysis 2021-02, Vol.11 (3), p.1863-1867
Main Authors: Kondo, Masaru, Nakamura, Kento, Krishnan, Chandu G, Takizawa, Shinobu, Abe, Tsukasa, Sasai, Hiroaki
Format: Article
Language:English
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Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.1c00057