Article ID Journal Published Year Pages File Type
5273365 Tetrahedron Letters 2010 5 Pages PDF
Abstract

The electroreductive intramolecular coupling of phthalimides with ketones in the presence of chlorotrimethylsilane gave five- and six-membered trans-cyclized products stereospecifically (>99%). Similar electroreductive intramolecular coupling of phthalimides with aldehydes afforded five-, six-, and seven-membered trans-cyclized products stereoselectively (75–93%). On the other hand, the reductive coupling of N-(oxoalkyl)phthalimides with samarium(II) iodide gave cis-cyclized products stereoselectively (88–>99%).

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Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry