174644-30-5Relevant academic research and scientific papers
Facile chemo-, regio-, and diastereoselective approach to cis-3,5-disubstituted γ-butyrolactones and fused γ-butyrolactones
Baag, Md. Merajuddin,Puranik, Vedavati G.,Argade, Narshinha P.
, p. 1009 - 1012 (2007)
(Chemical Equation Presented) Chemoselective SN2′ condensation of primary enolates of alkyl methyl ketones 2a-e with dimethyl bromomethylfumarate (1) followed by highly diastereoselective NaBH4 reduction of the ketone function in the
Dimethyl 2-(tosylmethyl)fumarate: An allyl sulfone as electrophilic reagent for the synthesis of itaconate ester derivatives
Chinchilla, Rafael,Galindo, Nuria,Najera, Carmen
, p. 1035 - 1046 (2007/10/03)
The reaction of dimethyl 2-(tosylmethyl)fumarate (6) prepared by iodosulfonylation-dehydroiodination of dimethyl itaconate, with carbonucleophiles or sodium methoxide allows the direct synthesis of 3-substituted itaconate ester derivatives 8 via a S(N)2' pathway. When sodium thiolates are used as nucleophiles dimethyl 2-(alkylthiomethyl)fumarates 9 or alkylthiomethylene butanoates 10 are obtained via a double S(N)2' process. In the case of pyrrolidine and cyclopentanone enamine, the corresponding diamino derivative 11 and the bicyclic[3.2.1]ketones 12 are obtained, respectively.
