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.
Lingua originale | Inglese |
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pagine (da-a) | 6624-6625 |
Numero di pagine | 2 |
Rivista | Journal of the American Chemical Society |
Volume | 132 |
Numero di pubblicazione | 19 |
DOI | |
Stato di pubblicazione | Pubblicato - 19 mag 2010 |
Pubblicato esternamente | Sì |