Journal
ORGANIC LETTERS
Volume 15, Issue 1, Pages 34-37Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol3029324
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Funding
- EPSRC [EP/F069103/1]
- AstraZeneca
- Engineering and Physical Sciences Research Council [EP/E02002X/1, EP/F069103/1] Funding Source: researchfish
- EPSRC [EP/F069103/1, EP/E02002X/1] Funding Source: UKRI
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In the presence of (-)-sparteine or a (+)-sparteine surrogate, organolithiums add to N-alkenyl-N'-arylureas to give benzylic organolithiums in an enantioselective manner. Under the influence of DMPU, these organolithiums undergo rearrangement with migration of the N'-aryl ring from N to C, leading to the urea derivatives of enantiomerically enriched amines bearing tertiary substituents. Basic hydrolysis returns the functionalized amine, providing a new synthetic route to compounds with quaternary stereogenic centers bearing nitrogen.
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