Organocatalytic Enantioselective Vinylogous Allylic Alkylation between β,γ-Unsaturated Pyrazoleamides and MBH Carbonates

Abstract

The direct asymmetric vinylogous allylic alkylation is an efficient method to construct chiral 1,5-diene compounds. In this work, acyclic unsaturated amides are used as a nucleophile for enantioselective vinylogous allylic alkylation. With 10 mol% of chiral tertiary amine C11, the enantioselective vinylogous allylic alkylation between β,γ-unsaturated pyrazoleamides and Morita-Baylis-Hillman carbonates is achieved, affording optically active multifunctional chiral 1,5-dienes in moderate to excellent yields (74-99%) with good-to-excellent enantioselectivities (67-94% ee).