Tandem β-alkylation-α-arylation of amines by carbolithiation and rearrangement of N -carbamoyl enamines (Vinyl Ureas)

Jonathan Clayden*, Morgan Donnard, Julien Lefranc, Alberto Minassi, Daniel J. Tetlow

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

52 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6624-6625
Number of pages2
JournalJournal of the American Chemical Society
Volume132
Issue number19
Early online date22 Apr 2010
DOIs
Publication statusPublished - 19 May 2010

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