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Light-controlled pKa value of chiral Brønsted acid catalysts in enantioselective aza-Friedel-Crafts reaction.
Krishnan, Chandu G; Kondo, Masaru; Yasuda, Osamu; Fan, Duona; Nakamura, Kento; Wakabayashi, Yoshitomo; Sasai, Hiroaki; Takizawa, Shinobu.
Afiliação
  • Krishnan CG; SANKEN, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan. taki@sanken.osaka-u.ac.jp.
  • Kondo M; Graduate School of Science and Engineering, Ibaraki University, Hitachi-shi, Ibaraki 316-8511, Japan. masaru.kondo.fg74@vc.ibaraki.ac.jp.
  • Yasuda O; SANKEN, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan. taki@sanken.osaka-u.ac.jp.
  • Fan D; SANKEN, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan. taki@sanken.osaka-u.ac.jp.
  • Nakamura K; SANKEN, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan. taki@sanken.osaka-u.ac.jp.
  • Wakabayashi Y; SANKEN, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan. taki@sanken.osaka-u.ac.jp.
  • Sasai H; SANKEN, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan. taki@sanken.osaka-u.ac.jp.
  • Takizawa S; Graduate School of Pharmaceutical Sciences, Osaka University, Suita-shi, Osaka, 565-0871, Japan.
Chem Commun (Camb) ; 59(66): 9956-9959, 2023 Aug 15.
Article em En | MEDLINE | ID: mdl-37526022
ABSTRACT
Bis(dithienylethene)-based BINOL-derived phosphoric acid (DTE-BPA) has been developed as a light-controlled chiral organocatalyst for the first time. The photoinduced modulation of the reactivity and selectivity via the open/close isomerization of the DTE scaffold led to superior light-controlled ability in the enantioselective aza-Friedel-Crafts reaction of aldimines with indoles. DFT studies showed that photoisomerization is accompanied by a shift of 1.1 pKa units between the open and closed isomers.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2023 Tipo de documento: Article
Texto completo
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XML
PubMed Links
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2023 Tipo de documento: Article