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Kinetic Resolution of Allyl Fluorides by Enantioselective Allylic Trifluoromethylation Based on Silicon‐Assisted CF Bond Cleavage
Author(s) -
Nishimine Takayuki,
Fukushi Kazunobu,
Shibata Naoyuki,
Taira Hiromi,
Tokunaga Etsuko,
Yamano Akihito,
Shiro Motoo,
Shibata Norio
Publication year - 2014
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.201308071
Subject(s) - allylic rearrangement , enantioselective synthesis , kinetic resolution , trifluoromethylation , cleavage (geology) , chemistry , silicon , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , materials science , trifluoromethyl , alkyl , fracture (geology) , composite material
Two birds, one stone! The first kinetic resolution of allyl fluorides was achieved by the development of an organocatalyzed enantioselective allylic trifluoromethylation. Two kinds of chiral fluorinated compounds, which incorporate C*F and C*CF 3 units, respectively, can thus be accessed by a single transformation.