Premium
Copper‐Catalyzed Enantioselective Formation of C−CF 3 Centers from β‐CF 3 ‐Substituted Acrylates and Acrylonitriles
Author(s) -
Poutrel Pauline,
Ivanova Maria V.,
Pannecoucke Xavier,
Jubault Philippe,
Poisson Thomas
Publication year - 2019
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.201904192
Subject(s) - enantioselective synthesis , chemistry , catalysis , copper , functional group , reaction mechanism , reaction conditions , combinatorial chemistry , medicinal chemistry , organic chemistry , polymer
The catalytic asymmetric synthesis of β‐trifluoromethylated esters or nitriles is reported. The use of an in situ formed chiral Cu−H complex allowed the enantioselective reduction of β‐trifluoromethylated acrylates or acrylonitriles. The reaction proceeds smoothly affording the corresponding enantioenriched products in good to excellent yields and outstanding enantioselectivities (up to 98 % ee ). The mechanism of the reaction was studied, and a plausible reaction pathway was suggested accordingly. Finally, the versatility of the products was highlighted through functional group manipulations.