Addition Reactions of Iodomethyllithium to Imines. A Direct and Efficient Synthesis of Aziridines and Enantiopure Amino Aziridines

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• 作者：José ; M. Concelló ; n ; Humberto Rodrí ; guez-Solla ; Carmen Simal
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：October 16, 2008
• 年：2008
• 卷：10
• 期：20
• 页码：4457-4460
• 全文大小：115K
• 年卷期：v.10,no.20(October 16, 2008)
• ISSN：1523-7052

文摘

An efficient and general synthesis of aziridines by the reaction of imines derived from p-toluenesulfonamides with in situ generated iodomethyllithium, with a simple and rapid experimental protocol, is reported for the first time. The reaction with the chiral aldimine derived from phenylalaninal allowed access to (2R,1′S)-2-(1′-aminoalkyl)aziridine with very high diastereoselectivity, in enantiopure form. A mechanism to explain this novel reaction is proposed.