title: A general route to mono- and disubstituted divinyl sulfones: acyclic Michael acceptors for the synthesis of polyfunctionalized cyclic sulfones.
abstract: Nucleophilic C-S bond formation using easily available β-hydroxysulfonate derivatives allowed direct access to new mono- and disubstituted divinyl sulfones. Our strategy uses thioethanol (HSCH(2)CH(2)OH) and its analogues such as HSCH(2)CH(Y)OH generated in situ. The strategy also allows the synthesis of modified divinyl sulfones attached to chiral appendages like carbohydrates. Bis-heteronucleophilic Michael addition reactions with 1 equiv of a primary amine afforded new generations of S,S-dioxothiomorpholine derivatives known for their therapeutic applications. Further synthetic manipulations of some of these cyclic compounds led to the synthesis of novel bicyclic derivatives.
authors: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721 302, India.
authors: Tarun Kumar
authors: TK
authors: Pal
authors: Santu
authors: S
authors: Dey
authors: Tanmaya
authors: T
authors: Pathak
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D013450:Sulfones