131822-89-4Relevant academic research and scientific papers
A study of the stereochemistry of the dealkoxycarbonylation of some sulfur-substituted cyclopropanes
Bernard, Angela M.,Piras, Pier P.,Cocco, Maria T.,Congiu, Cenzo,Onnis, Valentina
, p. 189 - 194 (2007/10/03)
2-sulfenyl- and 2-sulfonyl-phenyl groups can affect the stereochemistry of the products in the reaction of some ester-stabilized cyclopropyl carbanions.As these substituents are not particurarly effective chelating groups, the possibility of the intervention of a cis anomeric effect between the sulfur atom and the more extended orbital lobe of the cyclopropyl carbanion is considered.Evidences of the intermediacy of a pyramidal ester enolate are presented.The dimethyl 3-isopropyl-2-phenylsulfonyl-1,1-cyclopropane dicarboxylate 12 undergoes dealkoxycarbonylation,probably through a ring-opening ring-closure process, to give the corresponding monoester 15 with complete control of the relative stereochemistry of the three substituents.
Diastereoselctive Dealkoxycarbonylation of Sulfur-Substituted Dialkyl Cyclopropane-1,1-dicarboxylates
Bernard, Angela M.,Cerione, Giovanni,Piras, P. Paolo,Seu, Gianfranco
, p. 871 - 874 (2007/10/02)
In the dealkoxycarbonylation of dimethyl 2,2-dimethylcyclopropane-1,1-dicarboxylate, 3-alkylthio or 3-arylthio substituents induce moderate diastereoselection.The analogous dealkoxycarbonylation of 3-alkylsulfonyl- or 3-arylsulfonyl-substituted cyclopropa
