对映选择性氮杂傅-克反应中手性布朗斯特酸催化剂的光控p值
Light-controlled p value of chiral Brønsted acid catalysts in enantioselective aza-Friedel-Crafts reaction.
作者信息
Krishnan Chandu G, Kondo Masaru, Yasuda Osamu, Fan Duona, Nakamura Kento, Wakabayashi Yoshitomo, Sasai Hiroaki, Takizawa Shinobu
机构信息
SANKEN, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan.
Graduate School of Science and Engineering, Ibaraki University, Hitachi-shi, Ibaraki 316-8511, Japan.
出版信息
Chem Commun (Camb). 2023 Aug 15;59(66):9956-9959. doi: 10.1039/d3cc02719h.
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 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 p units between the open and closed isomers.
基于双（二噻吩乙烯）的联萘酚衍生磷酸（DTE-BPA）首次被开发为一种光控手性有机催化剂。DTE支架的开/关异构化对反应性和选择性的光诱导调节导致在醛亚胺与吲哚的对映选择性氮杂傅克反应中具有卓越的光控能力。密度泛函理论研究表明，光异构化伴随着开环和闭环异构体之间1.1个p单位的位移。
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