Stereocontrol in the Michael Reaction of Dimethyl Malonate with Alkyl 2-(1-Hydroxyalkyl)propenoates

Article abstract of DOI:10.1246/cl.1992.305

In this paper we show that the stabilized carbanion dimethyl malonate adds to alkyl 2-(1-hydroxyalkyl)propenoates under basic conditions.Side reactions, such as lactonization or elimination, may be reduced and/or completely avoided by the use of phase transfer catalysis.The high stereoselctivity associated with the additions discussed here was found to be under thermodynamic control.