Tetrahedron Letters

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

SB Boga, AB Alhassan, AB Cooper, NY Shih, RJ Doll

Index: Boga, Sobhana B.; Alhassan, Abdul-Basit; Cooper, Alan B.; Shih, Neng-Yang; Doll, Ronald J. Tetrahedron Letters, 2009 , vol. 50, # 38 p. 5315 - 5316

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Citation Number: 2

Abstract

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 ...