%0 Journal Article
%T Highly Regioselective Addition of Allylic Zinc Halides and Various Zinc Enolates to [1.1.1]Propellane.
%A Schwärzer K
%A Zipse H
%A Karaghiosoff K
%A Knochel P
%J Angew Chem Int Ed Engl
%V 59
%N 45
%D Nov 2020 2
%M 32744419
%F 16.823
%R 10.1002/anie.202009340
%X We report a range of highly regioselective openings of [1.1.1]propellane with various allylic zinc halides, as well as zinc enolates of ketones, esters and nitriles. The resulting zincated bicyclopentanes (BCPs) were trapped with a range of electrophiles including acyl chlorides, sulfonothioates, hydroxylamino benzoates, tosyl cyanide as well as aryl and allyl halides, generating highly functionalized BCP-derivatives. The unusually high regioselectivity of these reactions has been rationalized using DFT calculations. A bioisostere of the synthetic opioid pethidine was prepared in 95 % yield in one step using this method.