期刊
SYNTHESIS-STUTTGART
卷 53, 期 10, 页码 1795-1804出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1343-9451
关键词
sultam; isothiazolidine; tandem; nucleophilic substitution; Michael addition; cyclic sulfonamide; allyl bromide; stereoselective
资金
- Russian Federation [K-1073.2020.3]
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.
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.
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