Straightforward Route to γ-Sultams via Novel Tandem SN/Michael Addition

A novel tandem approach to trisubstituted gamma-sultams has been developed involving N-alkylation of methanesulfonanilides with EWG-substituted allyl bromides followed by intramolecular Michael addition. A series of various isothiazolidine 1,1-dioxides have been prepared under mild transition-metal-free conditions in high yields and trans-diastereoselectivity (confirmed by X-ray crystallography). The dependence of reactivity on electronic properties of substrates has been investigated.

Automated summary

A novel tandem approach has been developed for the synthesis of various isothiazolidine 1,1-dioxides. The method involves N-alkylation of methanesulfonanilides with EWG-substituted allyl bromides followed by intramolecular Michael addition, leading to high yields and trans-diastereoselectivity. The reactivity dependency on the electronic properties of substrates has been investigated.