Mukaiyama Aldol Addition

Schematic representation of the Mukaiyama Aldol Addition.
Mechanism of the Mukaiyama Aldol Addition
Mechanism of the Mukaiyama Aldol Addition
Sample reactions
intermediate structure
(CH2O)3, TiCl4
MeOH
-78 °C to RT, 16 h, 65%
intermediate structure
intermediate structure intermediate structure
i-PrOTiCl3
CH2Cl2
-78 to -40 °C, 4.5 h, 76%
intermediate structure
intermediate structure
TiCl2(Oi-Pr)2
CH2Cl2
-78 to 0 °C, 90 min
intermediate structure
intermediate structure intermediate structure
MgBr2.OEt2
PhMe
-15 °C, 75 min, 71%
"87 % yield based on 88 % conversion. Also isolated was the C2-epimer (16 % yield)."
intermediate structure
intermediate structure
CH2O, Yb(OTf)3
THF, H2O
RT, 3 d
intermediate structure