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Synlett 1999; 1999(4): 492-494
DOI: 10.1055/s-1999-2622
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Photodecarboxylative Addition of Carboxylates and α-Keto Carboxylates to Phthalimides

Axel G. Griesbeck* , Michael Oelgemöller
  • *Department of Organic Chemistry, Universität zu Köln, Greinstr. 4, D-50939 Köln, Germany; Fax 00 49 22 14 70 50 57; E-mail: griesbeck@uni-koeln.de
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Publication Date:
31 December 1999 (online)

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Intermolecular photoinduced decarboxylative additions of formate and a series of alkyl carboxylates as well as α-keto carboxylates to N-substituted phthalimides 1a-c and N-phthaloyl amino acid esters 3a-i gave hydroxy phthalimidines 2a-2j, 6a, b, 9 and hydroxy phthalimidine methyl esters 4a-4i in moderate to high yields. Only in one case (adamantane derivative 10) imide-catalyzed decarboxylation to give the corresponding hydrocarbon was observed.

photodecarboxylation - phthalimides - alkali metal carboxylates - α-keto carboxylates