Preparation and reductive transformations of vinylogous sulfonamides (β-sulfonyl enamines), and application to the synthesis of indolizidines

JP Michael, CB de Koning, TJ Malefetse…

Index: Michael, Joseph P.; De Koning, Charles R.; Malefetse, Tshepo J.; Yillah, Ibrahim Organic and Biomolecular Chemistry, 2004 , vol. 2, # 23 p. 3510 - 3517

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Citation Number: 16

Abstract

Condensation between the methiodide salts of 1-alkylpyrrolidine-2-thiones and ethyl [(4- methylphenyl) sulfonyl] acetate or 1-[(4-methylphenyl) sulfonyl] propan-2-one afforded several 2-{[(4-methylphenyl) sulfonyl] methylene} pyrrolidines in good yield. These β- sulfonyl enamines are sufficiently nucleophilic for cyclisation with internal electrophiles to give sulfone-substituted indolizines, potentially useful scaffolds for alkaloid synthesis. The ...