Dimethyl 2-(tosylmethyl)fumarate: An allyl sulfone as electrophilic reagent for the synthesis of itaconate ester derivatives

Article abstract of DOI:10.1016/0040-4020(95)00937-X

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.