1017952-97-4Relevant articles and documents
N,N′-diarylureas: A new family of atropisomers exhibiting highly diastereoselective reactivity
Clayden, Jonathan,Turner, Hazel,Helliwell, Madeleine,Moir, Elizabeth
, p. 4415 - 4423 (2008/09/21)
(Chemical Equation Presented) 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 addition 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.