Dieckmann Condensation

Schematic representation of the Dieckmann Condensation.
Mechanism of the Dieckmann Condensation
Mechanism of the Dieckmann Condensation
Sample reactions
intermediate structure
NaOMe
MeOH
Reflux, 20 min, 88%
intermediate structure
intermediate structure
i-Pr2NLi
THF
-78 °C, 40 min, 84%
intermediate structure
intermediate structure
KOt-Bu
Et2O
0 °C, 3 h
intermediate structure
intermediate structure intermediate structure
i-Pr2NLi
THF
-78 °C to RT, 3 h, 64-85%
intermediate structure
intermediate structure
TMS2NLi, TBSCl
THF, Hexane(s), HMPA
Reflux, 2.5 h
intermediate structure
intermediate structure
NaH
PhMe, MeOH
Reflux
intermediate structure
intermediate structure
NaOMe
PhMe
Reflux, , 33%
intermediate structure
intermediate structure
(CO2Me)2, NaH
DMF, MeOH
35-80 °C, , 44%
intermediate structure
intermediate structure
NaH
MeOH, DMF
RT to 155 °C, 20 min
intermediate structure