583827-30-9Relevant academic research and scientific papers
Asymmetric cyclopropanation of optically active vinyl sulfoxides: A new synthetic approach to biologically active compounds
Midura, Wanda H.
, p. 1285 - 1290 (2005)
The influence of adjacent substituents on stereochemical course of cyclopropanation of vinyl sulfoxides with stabilized and nonstabilized ylides, as well as dependence on reaction conditions, was investigated. Application of optically active cyclopropanes obtained in the synthesis of conformationally constrained analogs of L-glutamic acid, the useful pharmacological tools in investigation of excitatory amino acid receptors, is presented. Copyright Taylor & Francis Inc.
The first synthesis of enantiomerically pure cyclopropylphosphonate analogues of nucleotides via asymmetric cyclopropanation of chiral (1-diethoxyphosphoryl)vinyl p-tolyl sulfoxide
Midura, Wanda H.,Krysiak, Jerzy A.,Mikolajczyk, Marian
, p. 1245 - 1249 (2003)
(S)-(+)-(1-Diethoxyphosphoryl)vinyl p-tolyl sulfoxide undergoes cyclopropanation with ethyl (dimethylsulfuranylidene)acetate (EDSA) in a highly diastereoselective manner (facial stereoselectivity up to 12:1). The major diastereomer obtained in this reaction, (1S,2S)-(1-diethoxyphosphoryl-2-ethoxycarbonyl)cyclopropyl p-tolyl sulfoxide, was converted in three steps into enantiopure cyclopropylphosphonate analogues of purine nucleotides as the constrained forms of antiviral 1-alkenylphosphonic acid derivatives of purines.
Asymmetric synthesis of cyclopropyl phosphonates using chiral terpenyl sulfonium and selenonium ylides
Midura, Wanda H.,cianowski, Jacek,Banach, Anna,Zajc, Adrian
, p. 1488 - 1493 (2015/01/09)
The asymmetric cyclopropanation of a vinylphosphonate using optically active sulfonium and selenonium ylides derived from (-)-menthol and (+)-limonene was developed. The ylides were generated in situ by the reaction of the corresponding sulfonium or selenonium salt in the presence of potassium carbonate or DBU as a base. The transfer of the CHPh and CHCO2Et groups into the cyclopropane ring showed moderate diastereoselectivity and excellent enantioselectivity (up to 99:1) for the trans- and cis-products. The absolute configuration of phenyl cyclopropyl was assigned based on comparison to their tolyl analogues.
