Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 19, Pages 6624-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1007992
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Funding
- EPSRC
- AstraZeneca
- Engineering and Physical Sciences Research Council [EP/E057780/1] Funding Source: researchfish
- EPSRC [EP/E057780/1] Funding Source: UKRI
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Organolithiums add in an umpolung fashion to the beta-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.
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