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Lanthanum‐Catalyzed Enantioselective Trifluoromethylation by Using an Electrophilic Hypervalent Iodine Reagent
Author(s) -
Granados Albert,
Rivilla Iván,
Cossío Fernando P.,
Vallribera Adelina
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.201900598
Subject(s) - hypervalent molecule , trifluoromethylation , enantioselective synthesis , chemistry , electrophile , trifluoromethanesulfonate , reagent , catalysis , moiety , iodobenzene , ligand (biochemistry) , medicinal chemistry , trifluoromethyl , combinatorial chemistry , pyridinium , organic chemistry , alkyl , biochemistry , receptor
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 C 2 ‐symmetric ligands to generate intermediate La III 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 La III enolate by one unit of the C 2 ‐symmetric ligand.