Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 18, Pages 6859-6862Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0609834
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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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