Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines.
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.
Colyer
John T
JT
Chemistry Process Research and Development, Amgen Inc., Thousand Oaks, CA 91320-1799, USA.
Andersen
Neil G
NG
Tedrow
Jason S
JS
Soukup
Troy S
TS
Faul
Margaret M
MM
D001894:Borohydrides / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
D001894:Borohydrides; D007097:Imines; D013452:Sulfonium Compounds; C025364:sodium borohydride