TY - JOUR
T1 - β-Lactams or γ-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives
AU - Clayden, Jonathan
AU - Watson, David W.
AU - Helliwell, Madeleine
AU - Chambers, Mark
PY - 2003/10/21
Y1 - 2003/10/21
N2 - Substituted acrylamide derivatives of benzylamine are lithiated α to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a β-electron withdrawing group, 4-exo-trig cyclisation to a β-lactam.
AB - Substituted acrylamide derivatives of benzylamine are lithiated α to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a β-electron withdrawing group, 4-exo-trig cyclisation to a β-lactam.
UR - http://www.scopus.com/inward/record.url?scp=0142062462&partnerID=8YFLogxK
U2 - 10.1039/B308029C
DO - 10.1039/B308029C
M3 - Article (Academic Journal)
AN - SCOPUS:0142062462
SN - 1359-7345
VL - 9
SP - 2582
EP - 2583
JO - Chemical Communications
JF - Chemical Communications
IS - 20
ER -