Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines

…, NG Andersen, JS Tedrow, TS Soukup…

Index: Colyer, John T.; Andersen, Neil G.; Tedrow, Jason S.; Soukup, Troy S.; Faul, Margaret M. Journal of Organic Chemistry, 2006 , vol. 71, # 18 p. 6859 - 6862

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Citation Number: 75

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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