- (Diphenoxyphosphoryl)methyl p -tolyl sulfoxide: A new reagent for Z -selective synthesis of racemic and optically active vinyl sulfoxides
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Racemic and optically active (+)-(S)-(diphenoxyphosphoryl)methyl p-tolyl sulfoxide were prepared and used as Horner olefination reagents. Their reaction with aromatic and aliphatic aldehydes afforded the corresponding racemic and enantiomeric α,β-unsatura
- Midura, Wanda H.,Ewas, Ashraf M. Mohamed,Miko?ajczyk, Marian
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- Horner olefination reaction in organic sulfur chemistry and synthesis of natural and bioactive products
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This article outlines the results of our work on the application of the Horner olefination reaction for the synthesis of unsaturated sulfur compounds. A general synthesis of racemic and optically-active α,β-unsaturated sulfoxides by the Horner reaction with α-sulfinylmethylphosphonates as olefination reagents is presented. We demonstrated how the structure of the phosphonate moiety may control the E- and Z-stereoselectivity in the above reaction. The use of racemic and optically-active α- sulfinylvinylphosphonates in tandem Michael addition/Horner olefination reaction leads to a wide range of carbocyclic and heterocyclic vinyl sulfoxides. In second part of this account a new strategy for the synthesis of functionalized cyclopentenones is briefly described. The synthesis and reactivity of 3-phosphorylmethyl-cyclopentenones is discussed as a platform for developing the synthesis of racemic rosaprostol, enantiomeric prostaglandin B1 methyl esters, enantiopure isoterreins, natural and unnatural neplanocin A and enantiomeric forms of phytoprostane B1 type I. Copyright Taylor & Francis Group, LLC.
- Mikolajczyk, Marian,Midura, Wanda H.,Mohamed Ewas, Ashraf M.,Perlikowska, Wieslawa,Mikina, MacIej,Jankowiak, Aleksandra
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p. 313 - 325
(2009/04/06)
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