Triply Hydrogen‐Bond‐Directed Enantioselective Assembly of Pyrrolobenzo‐1, 4‐diazine Skeletons with Quaternary Stereocenters. Issue 25 (12th May 2015)

• Record Type: Journal Article
• Authors: Shen, Xiaoming; Wang, Yongtao; Wu, Tiandi; Mao, Zhenjun; Lin, Xufeng
• Is Part Of: Chemistry. Volume 21:Issue 25(2015)
• Page Start: 9039
• Page End: 9043
• Publication Date: 2015-05-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201500823
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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<italic>H</italic>‐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 CH⋅⋅⋅N hydrogen bonding to activate the substrate and induce chirality through a triple hydrogen‐bonding interaction.</p> </abstract>