Mukaiyama Aldol Addition

Schematic representation of the Mukaiyama Aldol Addition.
Mechanism of the Mukaiyama Aldol Addition
Mechanism of the Mukaiyama Aldol Addition
Original publication
Chem. Lett.. 1973, 2, 1011.
Reviews
Acc. Chem. Res.. 2000, 33, 432. Chem. Rev.. 1999, 99, 1095. Org. React.. 1994, 46, 1.
Sample reactions
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intermediate structure
(CH2O)3, TiCl4
MeOH
-78 °C to RT, 16 h, 65%
intermediate structure
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intermediate structure intermediate structure
i-PrOTiCl3
CH2Cl2
-78 to -40 °C, 4.5 h, 76%
intermediate structure
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intermediate structure
TiCl2(Oi-Pr)2
CH2Cl2
-78 to 0 °C, 90 min
intermediate structure
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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
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intermediate structure
CH2O, Yb(OTf)3
H2O, THF
RT, 3 d
intermediate structure