Synthesis of β-Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters
Toshimichi Kobayashi, Soshi Nishino, Masahiro Miura, Koji Hirano
Abstract
A copper-catalyzed silylamination of α,β-unsaturated esters with silylboranes and hydroxylamines has been developed to afford the corresponding β-silyl-α-amino acid derivatives, which are of great interest in medicinal and pharmaceutical chemistry. Additionally, by using a suitable chiral bisphosphine ligand, the asymmetric induction is possible, delivering the optically active β-silyl-α-amino acids with synthetically acceptable diastereomeric ratios (55:45-82:18 dr) and high enantiomeric ratios (81:19-99:1 er).
Topics & Concepts
ChemistryEnantioselective synthesisSilylationDiastereomerEnantiomerCatalysisAmino acidOptically activeLigand (biochemistry)Organic chemistryChiral ligandAsymmetric inductionStereochemistryReceptorBiochemistryAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisAdvanced Synthetic Organic Chemistry