Efficient synthesis of chiral γ-aminobutyric esters via direct rhodium-catalysed enantioselective hydroaminomethylation of acrylates

Anton Cunillera (1) , Miriam Díaz de Los Bernardos (2) , Martine Urrutigoity (3) , Carmen Claver (1) , Aurora Ruiz (1) , Cyril Godard (1)

1 Departament de Química Física i Inorganica, Universitat Rovira i Virgili
2 Universitat Rovira i Virgili
3 LCC - Laboratoire de chimie de coordination

The successful rhodium catalysed asymmetric intermolecular hydroaminomethylation (HAM) of alkenes using a single catalyst bearing the (R,R)-QuinoxP* ligand is reported. The HAM of α-alkyl acrylates is revealed to be an efficient tool for the regio- and enantioselective synthesis of γ-amino esters with ees up to 86%. HPNMR experiments provided insights into the reaction mechanism.

Domaines: Chimie de coordination

Anton Cunillera, Miriam Díaz de Los Bernardos, Martine Urrutigoity, Carmen Claver, Aurora Ruiz, et al.. Efficient synthesis of chiral γ-aminobutyric esters via direct rhodium-catalysed enantioselective hydroaminomethylation of acrylates. Catalysis Science & Technology, 2020, 10 (3), pp.630-634. ⟨10.1039/C9CY01797F⟩. ⟨hal-02877761⟩