An enamine controlling group for rhodium-catalyzed intermolecular hydroacylation

• DOI: 10.1016/j.tet.2018.04.068
• Publication Date: 2018-04-25T12:35:30Z
• Authors: Robert N. Straker; Michele Formica; James D. Lupton; Jingze Niu; Michael C. Willis
• Keywords: Hydroacylation; Enamine

Abstract An enamine-controlled hydroacylation of alkynes using a rhodium(I)/dppe catalyst system is described. The reaction is highly selective, forming the linear enaminone products as single regioisomers in all examples. In situ hydrolysis of the enamine functionality generated α-substituted 1,3-diketone products, and Lewis-acid mediated intramolecular conjugate addition of the hydroacylation products gave substituted hexahydroquinolones.