Asymmetric Synthesis of Dihydrocoumarins through Chiral Phosphoric Acid-Catalyzed Cycloannulation of <i>para</i>-Quinone Methides and Azlactones

Abstract

A chiral phosphoric acid-catalyzed approach constructing dihydrocoumarin motifs by the addition of azlactones to para-quinone methides (p-QMs) was developed. The reaction proceeded smoothly with a wide range of p-QMs and azlactones to generate corresponding products in high yields with excellent diastereoselectivities (>19:1 dr) and enantioselectivities (up to 99% ee). Two possible pathways were proposed to explain the stereoselectivity.