title: Highly Selective Addition of a Broad Spectrum of Trimethylsilane Pro-nucleophiles to N-tert-Butanesulfinyl Imines.
abstract: Addition of organotrimethylsilane reagents to chiral N-tert-butanesulfinyl imines can be achieved in good yields and with excellent diastereoselectivities by employing TMSO(-)/Bu4N(+) as a Lewis base activator in THF. A variety of aliphatic, aromatic, heteroaromatic and organometallic chiral imines were utilised as electrophiles for the synthesis of enantioenriched N-tert-butanesulfinyl amides. Remarkably, the same sets of reaction conditions could be used with a highly diverse range of bench-stable organotrimethylsilane reagents, which highlights the generality and robustness of this methodology.
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). donalfoshea@rcsi.ie.|School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4 (Ireland).. donalfoshea@rcsi.ie.
authors.forename: Donal F
authors.initials: DF
authors.lastname: O'Shea
keywords: chiral imines; diastereoselectivity; organotrimethylsilanes; pro-nucleophiles; trimethylsilyloxide activation