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 © 2007 American Chemical Society.
- TERT-BUTANESULFINYL KETIMINES
- CHIRAL AMINES