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KMID : 1059519940380120908
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Journal of the Korean Chemical Society
1994 Volume.38 No. 12 p.908 ~ p.914
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Synthesis of Octahydro-2,3-dioxo-cyclopenta[b]pyrrole-3a-carboxylates by Nucleophilic Addition to N-Acyliminium
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Seo Won-jun
Jung Chang-Hee
Choi Seung-Ju
Park Young-Kyu
Kim Tae-Heung
Lee Sang-Kyu
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Abstract
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6a-Hydroxy- and 6a-methoxy-derivatives (1∼6) of octahydro-2,3-dioxo-cyclopenta[b]-pyrrole-3a-carboxylate were synthesized from oxalylation of enamine A, which was prepared from condensation of five-membered cyclic β-keto ester and phenylalkylamine, followed by addition of water or methanol. The formation of heterocyclic ring was assumed to occur by the way of unstable N-acyliminium (B). Stable adduct C (1∼6) was obtained from nucleophilic addition to the endo-ene type pyrrolinium B.
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