Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines |
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Authors: | Colyer John T Andersen Neil G Tedrow Jason S Soukup Troy S Faul Margaret M |
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Institution: | Chemistry Process Research and Development, Amgen Inc., Thousand Oaks, CA 91320-1799, USA. |
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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. |
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