Photodecarboxylative additions of α-keto carboxylates to phthalimides alkylation, acylation and ring expansion

Griesbeck, Axel G., Oelgemoeller, Michael, and Lex, Johann (2000) Photodecarboxylative additions of α-keto carboxylates to phthalimides alkylation, acylation and ring expansion. Synlett, 2000 (10). pp. 1455-1457.

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Abstract

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.

Item ID: 29978
Item Type: Article (Research - C1)
ISSN: 1437-2096
Keywords: photodecarboxylation, phthalimides, α-keto carboxylates
Date Deposited: 21 Mar 2014 22:22
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 60%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 40%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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