71404-71-2Relevant academic research and scientific papers
ORGANOSELENIUM-INDUCED CYCLIZATIONS IN ORGANIC SYNTHESIS
Nicolaou, K.C.
, p. 4097 - 4109 (2007/10/02)
A number of organoselenium reagents are introduced as efficient initiators of ring closures leading from unsaturated substrates to lactones, cyclic ethers, cyclic thioethers, N-heterocycles and carbocycles.These cyclizations often proceed with high ring selectivity and stereoselectivity and are accompained by the incorporation of the phenylseleno group (PheSe) into the final product.Methods are described for the effective removal of this group (PheSe) by oxidation or reduction achieving unsaturation or saturation.Finally the successful application of this Se-based methodology to the synthesis of stable and biologically active prostacyclins is outlined.Representative experimental procedures are included.
Cyclofunctionalisation of unsaturated acids with benzeneselenenyl chloride. Kinetic and thermodynamic aspects of the rules for ring closure
Clive, Derrick L.J.,Russell, Charles G.,Chittattu, Gim,Singh, Alok
, p. 1399 - 1408 (2007/10/02)
Experimental procedures are described for the synthetically useful reaction by which olefinic acids are converted into lactones carrying a benzeneseleno-group. Data are presented to define some of the mechanistic details of this type of cyclofunctionalisation and kinetic and thermodynamic factors relevant to the Rules for Ring Closure are discussed. A nomenclature is introduced for a treatment of ring-fusion stereochemistry.
