Organocatalytic Asymmetric Michael Reactions of Cyclic N-Sulfonylimines with Nitroalkenes or 2-Nitroallylic Acetates

• DOI: 10.1021/acs.orglett.5c00753
• Publication Date: 2025-03-26T02:49:19Z
• Authors: Yurim Kim; Yeongju Kim; Sung-Gon Kim
• Keywords: Michael reaction

A highly efficient enantioselective Michael addition of cyclic N-sulfonylimines with nitroalkenes has been developed, utilizing a bifunctional squaramide catalyst. This approach achieves remarkable results, delivering products high yields and outstanding stereoselectivities, reaching up to 97% yield, >20:1 dr, >99% ee. Furthermore, an asymmetric tandem reaction 2-nitroallylic acetates established. innovative methodology involves Michael/intramolecular aza-Michael cascade, leading the formation enantioenriched benzosultam-fused tricyclic compounds excellent stereoselectivities (up dr ee).