TY - JOUR
T1 - Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas
AU - Clayden, Jonathan
AU - Dufour, Jérémy
AU - Grainger, Damian M.
AU - Helliwell, Madeleine
PY - 2007/6/20
Y1 - 2007/6/20
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=34250891292&partnerID=8YFLogxK
U2 - 10.1021/ja071523a
DO - 10.1021/ja071523a
M3 - Article (Academic Journal)
C2 - 17521189
AN - SCOPUS:34250891292
SN - 0002-7863
VL - 129
SP - 7488
EP - 7489
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 24
ER -