Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbonates

Abstract

An organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates with aromatic amines in the presence of -isocupreidine is described. Chiral allylic amines were obtained in almost quantitative yields (90-96%) with moderate enantioselectivity.

Recrystallization afforded products in good yields (45-73%) and high optical purity (82-99% ee). This method provides a facile and efficient route to obtain optically active -lactams, including the building block of the cholesterol-lowering drug Ezetimibe.

Keywords

• alkaloids
• allylic amination
• asymmetric synthesis
• Ezetimibe
• Morita–Baylis–Hillman carbonates
• organocatalysis