Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbonates­

Dedicated to Prof. Bäckvall to his 70th anniversary.

Abstract

An organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates with aromatic amines in the presence of β-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 β-lactams, including the building block of the cholesterol-lowering drug Ezetimibe.

Key words

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

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