Inside Cover: Catalytic Asymmetric Functionalization of Aromatic CH Bonds by Electrophilic Trapping of Metal-Carbene-Induced Zwitterionic Intermediates

Asymmetric functionalization of aromatic CH bonds of N,N-disubstituted anilines with diazo compounds and imines is reported for the efficient construction of α,α-diaryl benzylic quaternary stereocenters in good yields with high diastereoselectivities and excellent enantioselectivities. This Rh(II) /...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-11, Vol.53 (48), p.12974
Main Authors: Jia, Shikun, Xing, Dong, Zhang, Dan, Hu, Wenhao
Format: Article
Language:English
Online Access:Get full text
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Summary:Asymmetric functionalization of aromatic CH bonds of N,N-disubstituted anilines with diazo compounds and imines is reported for the efficient construction of α,α-diaryl benzylic quaternary stereocenters in good yields with high diastereoselectivities and excellent enantioselectivities. This Rh(II) /chiral phosphoric acid cocatalyzed transformation is proposed to proceed through a metal-carbene-induced zwitterionic intermediate which undergoes electrophilic trapping. To the best of our knowledge, this is the first asymmetric example of metal carbene-induced intermolecular functionalization of aryl CH bonds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201409113