ol5b00312_si_001.pdf (671.98 kB)
Cyclopentanone as a Cation-Stabilizing Electron-Pair Donor in the Calcium-Catalyzed Intermolecular Carbohydroxylation of Alkynes
journal contribution
posted on 2015-03-20, 00:00 authored by Tobias Stopka, Meike NiggemannAlthough
they have been used as reactivity-controlling additives
in cationic polymerizations for decades, Lewis basic “electron
pair donor” (ED) compounds were never used for the stabilization
of cationic intermediates in transformations of small molecules. As
such an ED, cyclopentanone proved highly efficient for the stabilization
of allyl and vinyl cations in combination with our calcium-based catalyst
system. Therefore, the first general transition-metal-free intermolecular
carbohydroxylation of alkynes with allyl and propargyl alcohols was
realized.