{Reference Type}: Journal Article
{Title}: Highly Regioselective Addition of Allylic Zinc Halides and Various Zinc Enolates to [1.1.1]Propellane.
{Author}: Schwärzer K;Zipse H;Karaghiosoff K;Knochel P;
{Journal}: Angew Chem Int Ed Engl
{Volume}: 59
{Issue}: 45
{Year}: Nov 2020 2
{Factor}: 16.823
{DOI}: 10.1002/anie.202009340
{Abstract}: 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.