Amines Bearing Tertiary Substituents by Tandem Enantioselective Carbolithiation–Rearrangement of Vinylureas

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 t...

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Bibliographic Details
Published in:Organic letters 2013-01, Vol.15 (1), p.34-37
Main Authors: Tait, Michael, Donnard, Morgan, Minassi, Alberto, Lefranc, Julien, Bechi, Beatrice, Carbone, Giorgio, O’Brien, Peter, Clayden, Jonathan
Format: Article
Language:English
Subjects:
Amines - chemistry
Catalysis
Lithium - chemistry
Molecular Structure
Sparteine - analogs & derivatives
Sparteine - chemistry
Stereoisomerism
Urea - chemistry
Vinyl Compounds - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3029324