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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.