General route to racemic and enantiomeric carbo- and heterocyclic vinyl sulfoxides via tandem Michael addition/Horner olefination of alpha-phosphorylvinyl sulfoxides.
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.
Mikołajczyk
Marian
M
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
Krysiak
Jerzy A
JA
Midura
Wanda H
WH
Wieczorek
Michał W
MW
Rózycka-Sokołowska
Ewa
E
D000475:Alkenes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013454:Sulfoxides / Q000138:chemical synthesis* / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D000475:Alkenes; D013454:Sulfoxides; D014753:Vinyl Compounds