{Reference Type}: Journal Article
{Title}: α-Cyclodextrin Encapsulation of Bicyclo[1.1.1]pentane Derivatives: A Storable Feedstock for Preparation of [1.1.1]Propellane.
{Author}: Matsunaga T;Kanazawa J;Ichikawa T;Harada M;Nishiyama Y;Duong NT;Matsumoto T;Miyamoto K;Uchiyama M;
{Journal}: Angew Chem Int Ed Engl
{Volume}: 60
{Issue}: 5
{Year}: 02 2021 1
{Factor}: 16.823
{DOI}: 10.1002/anie.202014997
{Abstract}: The bicyclo[1.1.1]pentane (BCP) scaffold is useful in medicinal chemistry, and many protocols are available for synthesizing BCP derivatives from [1.1.1]propellane. Here, we report (1) the α-cyclodextrin (α-CD) encapsulation of BCP derivatives, affording a stable, readily storable material from which BCPs can be easily and quantitatively recovered and (2) new and simple protocols for deiodination reaction of 1,3-diiodo BCP to afford [1.1.1]propellane in protic/aprotic/polar/non-polar solvents. The combination of these methodologies enables simple, on-demand preparation of [1.1.1]propellane in various solvents under mild conditions from α-CD capsules containing 1,3-diiodo BCP.