Synthesis of 3(2H)-furanones by the iron carbonyl-promoted cyclocoupling reaction of .ALPHA.,.ALPHA.'-dibromo ketones and carboxamides. A conventient route to muscarines.
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概要
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Reaction of α,α′-dibromo ketones and <I>N</I>,<I>N</I>-dimethylcarboxamides with the aid of Fe<SUB>2</SUB>(CO)<SUB>9</SUB> affords the corresponding reductive cyclocoupling products, 5-(dimethylamino)tetrahydro-3-furanones. In usual, the adducts derived from di-<I>s</I>-alkyl ketone dibromides easily eliminated dimethylamine to afford 3(2<I>H</I>)-furanones. <I>N</I>,<I>N</I>-Dimethylformamide (DMF), <I>N</I>,<I>N</I>-dimethylacetamide, <I>N</I>,<I>N</I>-dimethylbenzamide, and <I>N</I>-methylpyrrolidone have been used as dibromo ketone receptors. Thus, this general method provides a new, singleflask procedure for the preparation of the oxygen-containing five-membered ketones. The iron carbonyl-promoted 3+2 cyclocoupling reaction is interpreted as proceeding <I>via</I> a stepwise cycloaddition of a reactive 2-oxyallyl–Fe(II) intermediate and carboxamide. A facile conversion of such furanones to muscarine alkaloids is described.
- 公益社団法人 日本化学会の論文
著者
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Noyori Ryoji
Department Of Chemistry And Molecular Chirality Research Unit Nagoya University
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Makino Shinji
Department Of Cardiology Keio University School Of Medicine
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Makino Shinji
Department of Chemistry, Nagoya University
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Hayakawa Yoshihiro
Department of Chemistry, Faculty of Science, Nagoya University
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Takaya Hidemasa
Department of Chemistry, Nagoya University
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Hayakawa Norihiro
Department of Chemistry, Nagoya University
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