Amines Bearing Tertiary Substituents by Tandem Enantioselective Carbolithiation鈥揜earrangement of Vinylureas

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• 作者：Michael Tait ; Morgan Donnard ; Alberto Minassi ; Julien Lefranc ; Beatrice Bechi ; Giorgio Carbone ; Peter O鈥橞rien ; Jonathan Clayden
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：January 4, 2013
• 年：2013
• 卷：15
• 期：1
• 页码：34-37
• 全文大小：315K
• 年卷期：v.15,no.1(January 4, 2013)
• ISSN：1523-7052

文摘

In the presence of (鈭?-sparteine or a (+)-sparteine surrogate, organolithiums add to N-alkenyl-N鈥?arylureas to give benzylic organolithiums in an enantioselective manner. Under the influence of DMPU, these organolithiums undergo rearrangement with migration of the N鈥?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.