Journal
TETRAHEDRON
Volume 68, Issue 42, Pages 8805-8816Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.07.094
Keywords
Electroreduction; Reductive coupling; Chlorotrimethylsilane; Phthalimides; Alkylideneisoindolin-1-ones
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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 center dot 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. (C) 2012 Elsevier Ltd. All rights reserved.
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