title: Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines.
abstract: A variety of N-tert-butanesulfinyl imines were reduced with NaBH4 in THF containing 2% water to provide the corresponding secondary sulfinamides in high yield and diastereoselectivity. By using the same sulfinyl imine starting materials and changing the reductant to L-Selectride, the stereoselectivity could be efficiently reversed to afford the opposite product diastereomer in high yield and selectivity.
authors.affiliation: Chemistry Process Research and Development, Amgen Inc., Thousand Oaks, CA 91320-1799, USA.
authors.forename: John T
authors.initials: JT
authors.lastname: Colyer
authors.forename: Neil G
authors.initials: NG
authors.lastname: Andersen
authors.forename: Jason S
authors.initials: JS
authors.lastname: Tedrow
authors.forename: Troy S
authors.initials: TS
authors.lastname: Soukup
authors.forename: Margaret M
authors.initials: MM
authors.lastname: Faul
mesh_terms: D001894:Borohydrides / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D001894:Borohydrides; D007097:Imines; D013452:Sulfonium Compounds; C025364:sodium borohydride