Abstract
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 N2′ pathway. When sodium thiolates are used as nucleophiles dimethyl 2-(alkylthiomethyl)fumarates 9 or alkylthiomethylene butanoates 10 are obtained via a double S N2′ 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.
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