42882-30-4Relevant academic research and scientific papers
Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas
Clayden, Jonathan,Dufour, Jeremy,Grainger, Damian M.,Helliwell, Madeleine
, p. 7488 - 7489 (2008/02/11)
On lithiation, N-benzyl ureas varying N′-aryl substituents undergo a migration of the aryl ring to the ∞ carbon of the N-benzyl group. With chiral, enantiomerically pure N-∞-methylbenzyl ureas, the rearrangement is stereospecific and creates a new, fully substituted stereogenic center ∞ to N. Removal of the urea function by N-nitrosation and hydrolysis allows the synthesis of chiral tertiary carbinamines in high enantiomeric purity. Copyright
