75526-59-9Relevant 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.
Phenylselenoetherification. A Highly Efficient Cyclization Process for the Synthesis of O- and S-Heterocycles
Nicolaou, K. C.,Magolda, R. L.,Sipio, W. J.,Barnette, W. E.,Lysenko, Z.,Joullie, M. M.
, p. 3784 - 3793 (2007/10/02)
Phenylselenoetherification, a new cyclization procedure based on organoselenium chemistry, is described in detail.Unsaturated hydroxy and thio compounds were subjected to this new cyclization process to afford a series of phenyl selenoethers and phenyl selenothioethers which were transformed to a variety of heterocyclic systems by reductive or oxidative removal of the selenium group.Applications to the synthesis of muscarine analogues are described.
