Tandem β-Alkylation−α-Arylation of Amines by Carbolithiation and Rearrangement of N-Carbamoyl Enamines (Vinyl Ureas)

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• 作者：Jonathan Clayden ; Morgan Donnard ; Julien Lefranc ; Alberto Minassi ; Daniel J. Tetlow
• 刊名：Journal of the American Chemical Society
• 出版年：2010
• 出版时间：May 19, 2010
• 年：2010
• 卷：132
• 期：19
• 页码：6624-6625
• 全文大小：173K
• 年卷期：v.132,no.19(May 19, 2010)
• ISSN：1520-5126

文摘

Organolithiums add in an umpolung fashion to the β-carbon of N-carbamoyl enamines (N-vinyl ureas). The reaction proceeds with syn diastereospecificity and provides urea-stabilized, configurationally defined organolithiums. Facilitated by coordinating solvents (THF or DMPU), these undergo intramolecular attack on an N′-aryl group, resulting in retentive arylation of the organolithium and hence overall addition of an alkyl or aryl group to both carbon atoms of the urea-substituted alkene. Facile deprotection in hot butanol permits the rapid, multicomponent construction of heavily substituted amines.