Stereoselective Sulfa-Michael/Aldol Reaction Promoted by an Axially Chiral Styrene-Based Organocatalyst
Hao Yu, Zihao Li, Peng-Fei Lian, Quan‐Zhe Li, Yuan She, Zhi‐Gang Ma, Shu‐Yu Zhang
Abstract
Herein, we describe a stereoselective sulfa-Michael/aldol cyclization reaction promoted by a rationally designed novel axially chiral styrene-based organocatalyst. A variety of highly substituted tetrahydrothiophenes featuring an alkyne-substituted quaternary stereogenic center are obtained in good yields, excellent stereoselectivities, and exclusive trans selectivities. This process tolerates a broad range of alkynyl-substituted acrylamides under mind conditions. The utility of this approach is highlighted in its excellent asymmetric introduction, scalability, and attractive product diversification.
Topics & Concepts
StereocenterChemistryAldol reactionStereoselectivityStyreneAlkyneCombinatorial chemistryOrganic chemistryCatalysisEnantioselective synthesisCopolymerPolymerAxial and Atropisomeric Chirality SynthesisSulfur-Based Synthesis TechniquesAsymmetric Synthesis and Catalysis