Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 25, Pages 9039-9043Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500823
Keywords
BrOnsted acids; chirality; organocatalysis; phosphoric acids; Pictet-Spengler reaction
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Funding
- National Natural Science Foundation of China [21272202, J1210042]
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Highly efficient synthesis of optically enriched pyrrolobenzo-1,4-diazines bearing quaternary stereocenters has been realized through the chiral BrOnsted acid-catalyzed Pictet-Spengler reaction of 2-(1H-pyrrol-1-yl)anilines and -ketoamides in good to excellent yields and enantioselectivities. Computational studies suggest an unprecedented phenomenon whereby the chiral phosphoric acid catalyst employs attractive arene CHN hydrogen bonding to activate the substrate and induce chirality through a triple hydrogen-bonding interaction.
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