%0 Journal Article
%A Ramírez López, Pedro
%A Romero-Arenas, Antonio
%A Iglesias-Sigüenza, Javier
%A Fernández, Rosario
%A Ros, Abel
%A Lassaletta, José María
%T Axially Chiral N-Oxide Catalysts for the Allylation and Crotylation of Aromatic Aldehydes: Exploiting Nonlinear Effects
%D 2024
%U https://hdl.handle.net/20.500.14352/122845
%X A new family of IAN-type amine N-oxides is presented as catalysts for the allylation and crotylation of aromatic aldehydes with allyltrichlorosilanes. These reactions exhibit a remarkably positive nonlinear effect which enables the utilization of the catalysts in subenantiopure form. As enantiopure catalysts are not required under this regime, the synthesis of these N-oxides is straightforward through catalytic asymmetric synthesis, avoiding lengthy synthesis from the chiral pool or resolution of diastereoisomers. Studies of the corresponding crotylation with Z- and E-crotylsilanes suggest that the reaction proceeds through a chair-like transition state.
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