Photodecarboxylative additions of phenoxyacetates to N-methylphthalimide

Hatoum, Fadi, Gallagher, Sonia, and Oelgemöller, Michael (2009) Photodecarboxylative additions of phenoxyacetates to N-methylphthalimide. Tetrahedron Letters, 50 (47). pp. 6593-6596.

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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.

Item ID: 10226
Item Type: Article (Research - C1)
ISSN: 1873-3581
Keywords: photodecarboxylation; phthalimides; photochemistry; addition reactions; photoinduced electron transfer
Date Deposited: 13 Apr 2010 00:27
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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