Asymmetric Synthesis of anti-伪-Substituted 尾-Amino Ketones from Sulfinimines

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• 作者：Franklin A. Davis ; Peng Xu
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：May 6, 2011
• 年：2011
• 卷：76
• 期：9
• 页码：3329-3337
• 全文大小：935K
• 年卷期：v.76,no.9(May 6, 2011)
• ISSN：1520-6904

文摘

Previously unknown, enantiopure, 尾-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-伪-substituted 尾-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-伪-substituted isomers which did. The anti-伪-substituted 尾-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-伪-substituted 尾-amino esters because 伪-alkylation of N-sulfinyl 尾-amino Weinreb amide enolates resulted in poor diastereoselectivities.