Silyloxide-Promoted Diastereoselective Addition of Aryl and Heterocyclic Trimethylsilanes to <i>N</i>-<i>tert</i>-Butanesulfinylimines

The addition of a broad variety of substituted aromatic and heterocyclic silanes to chiral <i>N</i>-<i>tert-</i>butanesulfinylimines has been achieved providing 1,1-diaryl and diheterocyclic substituted sulfinamides with excellent diastereoselectivity in all cases. Employing Me₃SiO^–/Bu₄N⁺ as the Lewis base activator for silicon allowed a general procedure for all silane reagents, including the less reactive aromatic derivatives. Evidence that the diastereoselective additions occur via an open transition state is presented