Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals |
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| Authors: | Hikaru HasegawaHisanori Senboku Yoshinori KajizukaKazuhiko Orito Masao Tokuda |
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| Institution: | Laboratory of Organic Synthesis, Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan |
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| Abstract: | Tandem cyclization of N-propargylaminyl radicals, generated by N-chlorination of (E)-alk-4-enylamines 2a-d and 2f followed by treatment with tributyltin radical, afforded 2-methylenepyrrolizidines 3a-d and 3f in a highly stereoselective manner. A similar radical cyclization of (Z)-N-propargyl-1-methyl-5-phenylpent-4-enylamine (2e) gave pyrrolizidine 3b having the same stereochemistry as that obtained from the E isomer 2b. |
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| Keywords: | tandem radical cyclization aminyl radical pyrrolizidine N-chloroamine |
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