Reversal of Diastereofacial Selectivity in Hydride Reductions of N-tert-Butanesulfinyl Imines

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• 作者：John T. Colyer ; Neil G. Andersen ; Jason S. Tedrow ; Troy S. Soukup ; Margaret M. Faul
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：September 1, 2006
• 年：2006
• 卷：71
• 期：18
• 页码：6859 - 6862
• 全文大小：84K
• 年卷期：v.71,no.18(September 1, 2006)
• ISSN：1520-6904

文摘

A variety of N-tert-butanesulfinyl imines were reduced with NaBH₄ in THF containing 2% water toprovide the corresponding secondary sulfinamides in high yield and diastereoselectivity. By using thesame sulfinyl imine starting materials and changing the reductant to L-Selectride, the stereoselectivitycould be efficiently reversed to afford the opposite product diastereomer in high yield and selectivity.