Platinum-promoted cyclization reactions of amino olefins : II. Regio- and stereoselectivity in the cyclization reactions of C-methyl substituted pent-4-enylamines |
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Authors: | Juerg Ambuehl Paul S Pregosin Luigi M Venanzi Giambattista Consiglio Fiorella Bachechi Luigi Zambonelli |
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Institution: | Laboratorium für anorganische Chemie, ETH-Zentrum, CH-8092 Zürich Switzerland;Technisch-Chemisches Laboratorium, ETH-Zentrum, CH-8092 Zürich Switzerland;Laboratorio di Strutturistica Chimica “Giordano Giacomello”, Consiglio Nazionale delle Ricerche, C.P.N. 10, 00016-Monterotondo Stazione, Roma Italy |
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Abstract: | The compounds 1-, 2- and 3-methylpent-4 enylamine cyclize, in a reaction medium containing PtCl4]2-, to the corresponding cis- and trans-dimethylpyrrolidines showing marked regio and stereoselectivity effects. The following cyclization reactions are also reported: a) that of hex-4-enylamine which gives a mixture of 2-ethylpyrrolidine and 2-methylpiperidine, b) that of 2,2-dimethylpent-4-enylamine which produces 2,4,4-trimethylpyrrolidine and c) that of 2,2-dimethylhex-4-enylamine which results in the formation of 2-ethyl-4,4-dimethylpyrrolidine and 2-methyl-5,5-dimethylpiperidine.The X-ray crystal structures of trans-PtCl2(amine)(Et3P)] (amine = cis-2, 4-dimethylpyrrolidine and cis-2,3-dimethylpyrrolidine) are reported. |
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