Enantioselective Insertion of Carbenoids into N-H Bonds Catalyzed by Chiral Bicyclo Bisoxazoline Copper(I) Complexes

Paul Le Maux (1) , Gérard Simonneaux (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

Chiral copper(I)-bicyclobisoxazoline complexes were found to catalyse the insertion of α-diazocarbonyl compounds into N-H bonds of aniline derivatives. The insertion reactions proceeded with high yields (78-99%) and enantioselectivities of up to 81% for the different α-diazopropionates. A predominant effect of the nature and the position of the substituents on the enantiocontrol of the reaction was observed

Keywords: Chiral bisoxazoline; Copper; Enantioselectivity; N-H insertion catalysis

Domains: Chemical Sciences

Paul Le Maux, Gérard Simonneaux. Enantioselective Insertion of Carbenoids into N-H Bonds Catalyzed by Chiral Bicyclo Bisoxazoline Copper(I) Complexes. Tetrahedron, 2015, 71 (49), pp.9333-9338. ⟨10.1016/j.tet.2015.10.009⟩. ⟨hal-01216303⟩