title: Silyloxide-promoted diastereoselective addition of aryl and heterocyclic trimethylsilanes to N-tert-butanesulfinylimines.
abstract: The addition of a broad variety of substituted aromatic and heterocyclic silanes to chiral N-tert-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.
authors.affiliation: †Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland.
authors.forename: Manas
authors.initials: M
authors.lastname: Das
authors.affiliation: †Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland.|‡School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland.
authors.forename: Donal F
authors.initials: DF
authors.lastname: O'Shea
mesh_terms: D006571:Heterocyclic Compounds; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006571:Heterocyclic Compounds; C481933:N-tert-butanesulfinylimino ester; D010087:Oxides; D012821:Silanes; D013452:Sulfonium Compounds