Diastereoselective access to substituted oxetanes via 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 E-vinyl silane as a sole regioisomer. The application of the resultant vinyl silanes towards the diastereoselective synthesis of tetrasubstituted oxetanes is demonstrated.

Automated summary

The regio- and stereoselective hydrosilylation of various homopropargylic alcohols and their derivatives is discussed, which is tolerant towards different sterically and electronically substituted substrates and yields only the E-vinyl silane as the sole regioisomer. The application of the resulting vinyl silanes in the diastereoselective synthesis of tetrasubstituted oxetanes is demonstrated.