A review with 70 refs. LICKOR mixts. of organolithium reagents and bulky potassium alcoholates allow the smooth metalation and subsequent electrophilic substitution of low acidity hydrocarbons, in particular olefins. The allylpotassium intermediates exhibit peculiar conformational preferences which can be exploited in novel stereoselective carbon-carbon linking reactions. A few syntheses of simple natural products illustrate the method. A tentative explanation is given for the superior performance of LICKOR mixts. when compared with butylpotassium. [on SciFinder (R)]
Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ...
Jérôme Waser, Xingyu Liu, Nieves Pilar Ramirez Hernandez, Tobias Michael Milzarek