Asymmetric Allylic Amination of Morita-Baylis-Hillman Carbonates with Silylated tert-Butylhydroxycarbamate Derivatives

Abstract

The enantioselective amination of Morita-Baylis-Hill-man carbonates with silylated derivatives of tert-butylhydroxy-carbamates using beta-isocupreidine as an organocatalyst was investigated. The corresponding products were obtained in good yields with high enantioselectivities.

The scope and limitations of the reported protocol were explored, and representative transformations of the adducts toward heterocyclic compounds were highlighted.

Keywords

• alkaloids
• allylic compounds
• amination
• asymmetric synthesis
• organocatalysis