Synthesis of a Chiral Quaternary Carbon Center Bearing a Fluorine Atom: Enantio- and Diastereoselective Guanidine-Catalyzed Addition of Fluorocarbon Nucleophiles

The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was dem...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (20), p.3627-3631
Main Authors: Jiang, Zhiyong, Pan, Yuanhang, Zhao, Yujun, Ma, Ting, Lee, Richmond, Yang, Yuanyong, Huang, Kuo-Wei, Wong, Ming Wah, Tan, Choon-Hong
Format: Article
Language:English
Subjects:
asymmetric catalysis
fluorine
guanidine
Michael addition
transition states
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Summary:The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was demonstrated in the transition states resulting from the DFT results.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200900964