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Fluorinated Aromatic Ketones as Nucleophiles in the Asymmetric Organocatalytic Formation of CC and CN Bonds: A Facile Route to the Construction of Fluorinated Quaternary Stereogenic Centers
Author(s) -
Zhao Yujun,
Pan Yuanhang,
Liu Hongjun,
Yang Yuanyong,
Jiang Zhiyong,
Tan ChoonHong
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003761
Subject(s) - stereocenter , enantioselective synthesis , nucleophile , amination , chemistry , organic chemistry , nucleophilic aromatic substitution , combinatorial chemistry , nucleophilic substitution , catalysis
Highly enantioselective Mannich and α‐amination reactions have been successfully developed using α‐fluorinated aromatic ketones as fluorocarbon nucleophiles in the presence of a bicyclic chiral guanidine (see scheme; Ms=methanesulfonyl). This method is a simple and efficient approach to the construction of fluorinated quaternary stereogenic centers.