TY - JOUR
T1 - Lanthanum-Catalyzed Enantioselective Trifluoromethylation by Using an Electrophilic Hypervalent Iodine Reagent
AU - Granados, Albert
AU - Rivilla, Iván
AU - Cossío, Fernando P.
AU - Vallribera, Adelina
N1 - © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2019/6/21
Y1 - 2019/6/21
N2 - © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A highly enantioselective catalytic method for the synthesis of quaternary α-trifluoromethyl derivatives of 3-oxo esters is described. The reaction uses lanthanum(III) triflate and chiral PyBOX-type C2-symmetric ligands to generate intermediate LaIII complexes that incorporate an enolate moiety of the starting 3-oxo ester and the trifluoromethylation transfer reagent. The enantioselectivity of the reaction stems from the efficient blockage of one of the prochiral faces of the LaIII enolate by one unit of the C2-symmetric ligand.
AB - © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A highly enantioselective catalytic method for the synthesis of quaternary α-trifluoromethyl derivatives of 3-oxo esters is described. The reaction uses lanthanum(III) triflate and chiral PyBOX-type C2-symmetric ligands to generate intermediate LaIII complexes that incorporate an enolate moiety of the starting 3-oxo ester and the trifluoromethylation transfer reagent. The enantioselectivity of the reaction stems from the efficient blockage of one of the prochiral faces of the LaIII enolate by one unit of the C2-symmetric ligand.
KW - catalysis
KW - density functional calculations
KW - lanthanum
KW - PyBOX
KW - trifluoromethylation
UR - http://www.mendeley.com/research/lanthanumcatalyzed-enantioselective-trifluoromethylation-using-electrophilic-hypervalent-iodine-reag
U2 - 10.1002/chem.201900598
DO - 10.1002/chem.201900598
M3 - Article
C2 - 30897235
SN - 0947-6539
VL - 25
SP - 8214
EP - 8218
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 35
ER -