Pictet-Spengler Reaction

Mechanism of the Pictet-Spengler Reaction

Sample reactions


Dioxane , PhH
Reflux


H3PO4, NaIO4
Acetone, H2O
60-70 °C, 20 min, 60%



t-BuCO2H
PhMe
Reflux, 50 min, 53%
"Also isolated was the C3-epimer (37 % yield)."


HCl
H2O, THF
RT, 30 h, 92%



Cl2CHCO2H
PhMe
0 °C, 15 min, 100%


Me2S, CF3CO2H, PhSH, Cs2CO3
CH2Cl2
RT to 50 °C, 7.5 h, 84% (2 steps)



BzOH, Hydroquinone
Dean-Stark
PhH
Reflux, 10 h, 84%



BF3.OEt2
4 Å MS, Dean-Stark
PhMe
Reflux, 18 h


HCl
MeOH
RT, 30 h, 85%



AcOH, CH2Cl2
0 °C to RT, ON


Camphorsulfonic acid
PhMe
80 °C, , 69%



AcOH
PhMe
80 °C, 2 h, 26%
"Also isolated, 38 % isomer"
