Facile generation method for conjugated allenyl esters based on retro-Dieckmann-type ring-opening reactions |
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| Authors: | Shigeki Sano |
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| Institution: | Graduate School of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan |
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| Abstract: | α-Alkynyl-α-ethoxycarbonyl cyclopentanones 1a-c and cyclohexanones 2a-c were readily synthesized by the reaction of ethyl 2-oxocyclopentanonecarboxylate 6 and ethyl 2-oxocyclohexanonecarboxylate 7 with alkynyllead triacetates 5a-c obtained from lithium acetylides 4a-c and lead tetraacetate. Treatment of 1a-c and 2a-c with 1 N KOH in THF or with n-Bu4N+OEt− in EtOH and THF gave the corresponding conjugated allenyl esters 8a-c, 9a-c, 10a-c, and 11a-c in good to excellent yields, respectively. |
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| Keywords: | Cyclopentanone Cyclohexanone Retro-Dieckmann reaction Conjugated allenyl ester X-ray crystallographic analysis |
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