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N,N'-Diarylureas: A New Family of Atropisomers Exhibiting Highly Diastereoselective Reactivity.

  作者 Clayden, Jonathan;Turner, Hazel;Helliwell, Madeleine;Moir, Elizabeth;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-12;  页码  4415-4423  
  关联知识点  
 

[摘要]2,6-Disubstituted N-aryl ureas rotate slowly about their Ar-N bonds and can exist as separable atropisomers. They also react remarkably diastereoselectively, with the urea axis controlling new stereogenic centers with high fidelity in a variety of nucleophilic and electrophilic addn. reactions. The sense of diastereoselectivity in lateral lithiation-electrophilic quench reactions is electrophile-dependent and appears to be the result of stereospecific reaction with one of two interconvertible diastereoisomeric organolithiums.

 
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