Stereoselective syntheses of 1,2-dialkyl-1-phenyl cyclopentanes involving intramolecular carbolithiation of α-thioalkenes
作者:Alain Krief、Benoît Kenda、Bruno Remacle
DOI:10.1016/0040-4020(96)00261-x
日期:1996.5
2-Ethyl-1-methyl-1-phenyl cyclopentane, unavailable by butyllithium-promoted carbocyclisation of the corresponding alkenyl selenide, has been synthesized from 6-methylseleno-6-phenyl-1-phenylthio-1-heptene and 7-methylseleno-7-phenyl-2-phenylthio-2-octene with high stereocontrol at all the three stereogenic centers. Depending upon the solvent used, the derivative in which the methyl- and the phenylthiomethyl
Synthesis of organolithium compounds from phenyl selenides
作者:Alain Krief、Abdesslame Nazih、Myriam Hobe
DOI:10.1016/0040-4039(95)01689-f
日期:1995.10
Alkyl aryl selenides react with lithium arenides to produce, regioselectively, alkyllithiums and lithium arylselenolates. Experimental conditions, especially the temperature, have a profound effect on the course of this reaction and on the nature of the products.
2-Ethyl-1-methyl-1-phenyl cyclopentane, unavailable by butyllithium-promoted carbocyclisation of the corresponding alkenyl selenide, has been efficiently produced using two different strategies involving the carbocyclisation of 6-phenyl-6-methylseleno-1-heptene as the key step.