Electroreductive intermolecular coupling of phthalimides with aldehydes: application to the synthesis of alkylideneisoindolin-1-ones |
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Authors: | Naoki Kise Shinsaku Isemoto Toshihiko Sakurai |
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Affiliation: | Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-cho Minami, Tottori 680-8552, Japan |
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Abstract: | The electroreduction of N-methyl, N-p-anisyl, and N-unsubstituted phthalimides with aldehydes in the presence of chlorotrimethylsilane and triethylamine gave intermolecularly coupled products, 3-hydroxy-3-(1-hydroxyalkyl)isoindolin-1-ones. The coupling products were reduced with Et3SiH/BF3·Et2O to 3-(1-hydroxyalkyl)isoindolin-1-ones, which were dehydrated to alkylideneisoindolin-1-ones. From N-unsubstituted phthalimides, Z-isomers of alkylideneisoindolin-1-ones were obtained stereospecifically. |
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