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Synthesis of a Chiral Quaternary Carbon Center Bearing a Fluorine Atom: Enantio‐ and Diastereoselective Guanidine‐Catalyzed Addition of Fluorocarbon Nucleophiles
Author(s) -
Jiang Zhiyong,
Pan Yuanhang,
Zhao Yujun,
Ma Ting,
Lee Richmond,
Yang Yuanyong,
Huang KuoWei,
Wong Ming Wah,
Tan ChoonHong
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200900964
Subject(s) - chemistry , fluorine , bifunctional , guanidine , nucleophile , catalysis , fluorocarbon , adduct , stereoselectivity , carbon fibers , carbon atom , quaternary carbon , atom (system on chip) , medicinal chemistry , computational chemistry , stereochemistry , enantioselective synthesis , organic chemistry , ring (chemistry) , materials science , composite number , computer science , composite material , embedded system
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.