The current utility and future potential of multiborylated alkanes.

Organoboron chemistry has become a cornerstone of modern synthetic methodology. Most of these reactions use an organoboron starting material that contains just one C(sp)-B or C(sp)-B bond; however, there has been a recent and accelerating trend to prepare multiborylated alkanes that possess two or more C(sp)-B bonds. This is despite a lack of general reactivity, meaning many of these compounds currently offer limited downstream synthetic value.

Diastereoselective access to substituted oxetanes hydrosilylation-iodocyclisation of homopropargylic alcohols.

The regio and stereoselective hydrosilylation of a variety of homopropargylic alcohols and their derivatives is described. The reaction is tolerant to a variety of sterically and electronically varied substrates, affording only the -vinyl silane as a sole regioisomer. The application of the resultant vinyl silanes towards the diastereoselective synthesis of tetrasubstituted oxetanes is demonstrated.

Regioselective Synthesis of Multifunctional Allylic Amines; Access to Ambiphilic Aziridine Scaffolds.

We describe, for the first time, a highly regioselective hydrosilylation of propargylic amines. The reaction utilizes a PtCl/XantPhos catalyst system to deliver hydrosilanes across the alkyne to afford multifunctional allylic amines in high yields. The reaction is tolerant to a wide variety of functional groups and provides high value intermediates with two distinct functional handles.