Selective Functionalization of Achmatowicz Rearrangement Products by Reactions with Potassium Organotrifluoroborates under Transition-Metal-Free Conditions

Abstract

The repertoire of synthetic transformations of the products of the Achmatowicz rearrangement has been expanded by exploring their reactivity with potassium organotrifluoroborates in the absence of transition metals. Depending on the reaction conditions and the substitution pattern of the starting material, the reaction may lead to the stereoselective synthesis of dihydropyranones (2,6- trans), tetrahydropyranones (2,3- cis-2,6- cis) or functionalized 1,4-dicarbonyl compounds. The method has also been adapted for the one-pot synthesis of functionalized pyrroles.