Synfacts 2009(12): 1360-1360  
DOI: 10.1055/s-0029-1218246
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Three-Component Vinylogous Mannich Reaction

Contributor(s): Mark Lautens, Chit Tsui
P. Hermange, M. E. T. H. Dau, P. Retailleau, R. H. Dodd*
Institut de Chimie des Substances Naturelles, Gif-sur-Yvette, France
Further Information

Publication History

Publication Date:
20 November 2009 (online)


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.