Diastereoselective Three-Component Vinylogous Mannich Reaction

Abstract

Tetrahydroisoquinolines and 1,2-dihydroisoquinolines represent the core structure of various alkaloids and pharmaceutical products. Continuing efforts have focused on gaining access to the optically pure C1-substituted derivatives. The authors report a three-component vinylogous Mannich reaction of an isoquinoline, a silyloxyfuran, and an acyl or sulfonyl chloride to obtain a variety of isoquinolinobutyrolactones in excellent yields and diastereoselectivities. The products can be further utilized to synthesize the core structure of emetine, an antitumor alkaloid.