title: General route to racemic and enantiomeric carbo- and heterocyclic vinyl sulfoxides via tandem Michael addition/Horner olefination of alpha-phosphorylvinyl sulfoxides.
abstract: A new one-pot synthesis of heterocyclic and carbocyclic vinyl sulfoxides has been developed which involves reaction of alpha-phosphorylvinyl sulfoxides with carbonyl compounds bearing oxygen, nitrogen, and carbon nucleophilic centers. Use of optically active alpha-phosphorylvinyl p-tolyl sulfoxides in this tandem Michael addition/Horner olefination reaction leads to the corresponding optically active cyclic sulfoxides. In this way, a variety of optically active chromene, pyrrolizine, chinoline, and cyclopentene sulfoxides have been efficiently prepared.
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, 90-363 Lodz Sienkiewicza 112, Poland. marmikol@bilbo.cbmm.lodz.pl
authors.forename: Marian
authors.initials: M
authors.lastname: Mikołajczyk
authors.forename: Jerzy A
authors.initials: JA
authors.lastname: Krysiak
authors.forename: Wanda H
authors.initials: WH
authors.lastname: Midura
authors.forename: Michał W
authors.initials: MW
authors.lastname: Wieczorek
authors.forename: Ewa
authors.initials: E
authors.lastname: Rózycka-Sokołowska
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013454:Sulfoxides / Q000138:chemical synthesis* / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000475:Alkenes; D013454:Sulfoxides; D014753:Vinyl Compounds