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

  作者 TAIT MICHAEL; DONNARD MORGAN; MINASSI ALBERTO; LEFRANC JULIEN; BECHI BEATRICE; CARBONE GIORGIO; OBRIEN PETER; CLAYDEN JONATHAN  
  选自 期刊  Organic Letters;  卷期  2013年15-1;  页码  34-37  
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[摘要]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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