Synthesis of Furan Derivatives. XLV. A New Acid catalyzed Cyclization of sterically Hindered cis Alkenals
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概要
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Preparation of aryl 2,4-dialkyl-2,4-pentadienals (aryl is (5-nitro-2-furyl)- or (5-nitro-2-thienyl)-, alkyl is methyl or ethyl) by condensation of alkyl enol ether R-CH=CH-OR R〓H) with aryl-α-alkylated acrolein acetals gave stereoselectively 2-cis-4-trans-2,4-dialkylated pentadienals. Driving force leading to above configuration is overcrawding control of the sterically hindered chain. The stereoselective formation of cis-alkenals was found to be applicable for aryl 2-cis-4-cis-6-trans-trialkylated heptatrienal. All hindered cis alkenals prepared in this paper cyclized to five or seven membered cyclic ketones in the presence of HCl or some organic acids. A mechanism for the cyclization was proposed, that involves initial formation of oxocarbonium ion, which is later transformed by two of successive processes, i.e., the formation of bicyclo-[2.1.0] cyclopentanone derivative and its ring rupture by acid. Proposed mechanism was discussed from the result of deuterohydrochloric acid incorporated cyclization of IVa.
- 社団法人日本薬学会の論文
- 1969-09-25
著者
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佐藤 勝利
Faculty Of Pharmaceutical Sciences Kyushu University
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西海枝 東雄
Faculty of Pharmaceutical Sciences, Kobe Gakuin University
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小川 晴
Faculty of Pharmaceutical Sciences, Kyushu University
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小川 晴
Faculty Of Pharmaceutical Sciences Kyushu University
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西海枝 東雄
Faculty Of Pharmaceutical Sciences Kobe Gakuin University
関連論文
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