TY - JOUR AU - Klochkova, Anastasiia; Bubyrev, Andrey; Dar’in, Dmitry; Bakulina, Olga; Krasavin, Mikhail; Sokolov, Viktor TI - Straightforward Route to γ-Sultams via Novel Tandem SN/Michael Addition SN - 0039-7881 SN - 1437-210X PY - 2021 JO - Synthesis JF - Synthesis LA - EN VL - 53 IS - 10 SP - 1795 EP - 1804 DA - 2021/01/25 ET - 2020/12/29 KW - sultam KW - isothiazolidine KW - tandem KW - nucleophilic substitution KW - Michael addition KW - cyclic sulfonamide KW - allyl bromide KW - stereoselective AB - A novel tandem approach to trisubstituted γ-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. PB - Georg Thieme Verlag KG DO - 10.1055/a-1343-9451 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/a-1343-9451 ER -