Stereoselective Sulfa-Michael/Aldol Reaction Promoted by an Axially Chiral Styrene-Based Organocatalyst

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.

Automated summary

This study describes a stereoselective sulfa-Michael/aldol cyclization reaction using a novel axially chiral styrene-based organocatalyst. The reaction successfully produces highly substituted tetrahydrothiophenes with an alkyne-substituted quaternary stereogenic center. The reaction tolerates a wide range of alkynyl-substituted acrylamides and shows excellent asymmetric introduction, scalability, and product diversification.