N,N '-diarylureas: A new family of atropisomers exhibiting highly diastereoselective reactivity

作者:Clayden Jonathan*; Turner Hazel; Helliwell Madeleine; Moir Elizabeth
来源:Journal of Organic Chemistry, 2008, 73(12): 4415-4423.
DOI:10.1021/jo702706c

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 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.

  • 出版日期2008-6-20