209809-54-1Relevant academic research and scientific papers
Asymmetric cyclopropanation of optically active (1-diethoxyphosphoryl)vinyl p-tolyl sulfoxide with sulfur ylides: A rationale for diastereoselectivity
Midura, Wanda H.,Krysiak, Jerzy A.,Cypryk, Marek,Mikolajczyk, Marian,Wieczorek, Michal W.,Filipczak, Agnieszka D.
, p. 653 - 662 (2007/10/03)
The title sulfoxide (S)-(+)-1a was found to react with sulfur ylides affording the corresponding cyclopropanes in high yields. With fully deuterated dimethyl(oxo)sulfonium methylide, (CD3)2S(O)CD 2, the cyclopropanation re
1,3-dipolar cycloaddition of diazoalkanes to racemic and optically active α-(diethoxyphosphoryl)vinyl p-tolyl sulfoxides: A new synthesis of 3- phosphorylpyrazoles and asymmetric synthesis of cyclopropanes
Midura, Wanda H.,Krysiak, Jerzy A.,Mikolajczyk, Marian
, p. 14791 - 14802 (2007/10/03)
Cycloaddition of diazomethane and ethyl diazoacetate to α- (diethoxyphosphoryl)vinyl p-tolyl sulfoxide 1a and its β-substituted analogues (Me, Ph) results in the formation of 3-phosphorylpyrazoles in high yield. The reaction of chiral (S)-(+)-1a with diphenyldiazomethane proceeds fully diastereoselectively to give the corresponding cyclopropane (+)-6a with the (S(C), S(S)) configuration determined by X-ray diffraction analysis. Diazopropane reacts with (S)-(+)-1a to give only one diastereoisomer of the pyrazoline cycloadduct (+)-2e which undergoes decomposition to the cyclopropane (+)-6b with preservation of configurational integrity.
