TY - JOUR
T1 - Fast racemisation and slow epimerisation of laterally lithiated amides
T2 - Stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums
AU - Clayden, Jonathan
AU - Stimson, Christopher C.
AU - Keenan, Martine
AU - Wheatley, Andrew E H
PY - 2004/1/21
Y1 - 2004/1/21
N2 - Tertiary 1-naphthamides racemise much more slowly than their laterally lithiated derivatives, and the relative rates of racemisation and epimerisation of these derivatives indicate that the lithium-bearing stereogenic centre inverts via a "conducted tour" mechanism, in which the lithium cation is delivered from one face to the other by coordination to the rotating amide group.
AB - Tertiary 1-naphthamides racemise much more slowly than their laterally lithiated derivatives, and the relative rates of racemisation and epimerisation of these derivatives indicate that the lithium-bearing stereogenic centre inverts via a "conducted tour" mechanism, in which the lithium cation is delivered from one face to the other by coordination to the rotating amide group.
UR - http://www.scopus.com/inward/record.url?scp=1642439222&partnerID=8YFLogxK
U2 - 10.1039/B310963A
DO - 10.1039/B310963A
M3 - Article (Academic Journal)
AN - SCOPUS:1642439222
SN - 1359-7345
VL - 10
SP - 228
EP - 229
JO - Chemical Communications
JF - Chemical Communications
IS - 2
ER -