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

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Abstract
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 stereoselectivity associated with the additions discussed here was found to be under thermodynamic control.