Article ID Journal Published Year Pages File Type
5281890 Tetrahedron Letters 2009 4 Pages PDF
Abstract

Photoaddition of various phenoxyacetates to N-methylphthalimide affords the corresponding hydroxyphthalimidines in yields of 21-93%. The diastereoselectivity of the intermolecular addition is studied for a series of 2-substituted phenoxyacetates with low diastereoselectivities being observed. Comparison experiments with anisole and ether-containing phthalimide confirm that the crucial electron-transfer step occurs from the carboxylate functionality.

Graphical abstractPhotoaddition of various phenoxyacetates to N-methylphthalimide affords the corresponding hydroxyphthalimidines in yields of 21-93%. The diastereoselectivity of the intermolecular addition is studied for a series of 2-substituted phenoxyacetates with low diastereoselectivities being observed. Comparison experiments with anisole and ether-containing phthalimide confirm that the crucial electron-transfer step occurs from the carboxylate functionality.Download full-size image

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Physical Sciences and Engineering Chemistry Organic Chemistry
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