Triply Hydrogen‐Bond‐Directed Enantioselective Assembly of Pyrrolobenzo‐1,4‐diazine Skeletons with Quaternary Stereocenters | Zendy

Shen Xiaoming | Zendy; Wang Yongtao | Zendy; Wu Tiandi | Zendy; Mao Zhenjun | Zendy; Lin Xufeng | Zendy

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Triply Hydrogen‐Bond‐Directed Enantioselective Assembly of Pyrrolobenzo‐1,4‐diazine Skeletons with Quaternary Stereocenters

Author(s) -

Shen Xiaoming,

Wang Yongtao,

Wu Tiandi,

Mao Zhenjun,

Lin Xufeng

Publication year - 2015

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201500823

Subject(s) - stereocenter , enantioselective synthesis , hydrogen bond , diazine , catalysis , chemistry , phosphoric acid , chirality (physics) , brønsted–lowry acid–base theory , stereochemistry , substrate (aquarium) , combinatorial chemistry , organic chemistry , molecule , chiral symmetry , biology , ecology , nambu–jona lasinio model , physics , quantum mechanics , quark

Highly efficient synthesis of optically enriched pyrrolobenzo‐1,4‐diazines bearing quaternary stereocenters has been realized through the chiral Brønsted acid‐catalyzed Pictet–Spengler reaction of 2‐(1 H ‐pyrrol‐1‐yl)anilines and α‐ketoamides in good to excellent yields and enantioselectivities. Computational studies suggest an unprecedented phenomenon whereby the chiral phosphoric acid catalyst employs attractive arene CH⋅⋅⋅N hydrogen bonding to activate the substrate and induce chirality through a triple hydrogen‐bonding interaction.

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