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Synlett 2000; 2000(10): 1455-1457
DOI: 10.1055/s-2000-7623
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Photodecarboxylative Additions of α-Keto Carboxylates to Phthalimides Alkylation, Acylation and Ring Expansion

Axel G. Griesbeck* , Michael Oelgemöller, Johann Lex
  • *Department of Organic Chemistry, Universität zu Köln, Greinstr. 4, 50939 Köln, Germany; Fax + 0049 22 14 70 50 57; E-mail: griesbeck@uni-koeln.de
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Publication Date:
31 December 2000 (online)

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The influence of the substitution pattern on reactivity and selectivity of the photodecarboxylative addition of α-keto carboxylates to N-methyl phthalimide was investigated. Secondary and tertiary α-keto carboxylates as well as glyoxylate gave alkylation and reduction products 2a-d, respectively. Pyruvate and the α-keto leucine anion both gave the ring expansion products 3e and 3f. In the latter case the acylation product 4e was additionally isolated.

photodecarboxylation - phthalimides - α-keto carboxylates