[3+2] Cycloaddition-mediated synthesis of 3-methylsulfanyl-pyrrolidine-3-carboxylic acid methyl ester

• Published in: Tetrahedron letters Vol. 50; no. 38; pp. 5315 - 5316
• Main Authors: Boga, Sobhana B., Alhassan, Abdul-Basit, Cooper, Alan B., Shih, Neng-Yang, Doll, Ronald J.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 23-09-2009
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2009.06.141

Montmorollonite K-10 was found to be an efficient catalyst for the [3+2] annulation of thiomethylacrylate
2 and azomethine ylide precursor
3 towards the synthesis of novel 3-methylsulfanyl-pyrrolidine
4.
1,3-Dipolar cycloaddition reactions are fundamental processes in organic chemistry. Herein we report [3+2] annulation of thiomethylacrylate
2 and azomethine ylide precursor
3 towards the synthesis of novel 3-methylsulfanyl-pyrrolidine
5. Alternatively, we have also explored the alkylation of
7 with dimethyldisulfide/LDA for the introduction of thiomethyl group towards the synthesis of
5 in moderate to good yields. Efficacy of these two routes under various conditions/catalysts for the synthesis of
5 is presented.