Enantioselective Construction of Vicinal Sulfur‐functionalized Quaternary and Tertiary Stereocenters via Organocatalytic Michael Addition of 5<i>H</i>‐Thiazol‐4‐ones to 1‐Azadienes
Fushuai Li, Chen Zhang, Yuyu Cheng, Qianfa Jia, Wenjun Li, Kun Liu, Pengfei Li
Abstract
Abstract An organocatalytic enantioselective Michael addition of 5 H ‐thiazol‐4‐ones to 1‐azadienes has been developed. In the presence of chiral phosphoric acid, a series of optically active benzofuran derivatives featured by vicinal sulfur‐containing quaternary and tertiary stereocenters were obtained in high yields (71‐99%) with high stereoselectivities (70–96% ee and 8 : 1–20 : 1 d.r.).
Topics & Concepts
StereocenterEnantioselective synthesisChemistryMichael reactionVicinalOrganocatalysisPhosphoric acidSulfurOrganic chemistryStereochemistryOptically activeCatalysisSulfur-Based Synthesis TechniquesAsymmetric Synthesis and CatalysisAdvanced Synthetic Organic Chemistry