139669-41-3Relevant academic research and scientific papers
The synthesis and some manipulations of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates
Lawrence, Ron M.,Perlmutter, Patrick
, p. 839 - 845 (1996)
A new, one-pot annulation process, involving conjugate addition of the sodium salts of dimethyl (or dibenzyl) malonate to alkyl 2-(l-hydroxyalkyl)propenoates, produces a mixture of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates. Alkylations of the cis-isomers were found to be highly stereoselective. The introduction of unsaturation into these molecules is also described.
Stereocontrol in the Michael Reaction of Dimethyl Malonate with Alkyl 2-(1-Hydroxyalkyl)propenoates
Lawrence, Ronnie,Perlmutter, Patrick
, p. 305 - 308 (2007/10/02)
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.
