Copper(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of N-Methyltetrahydropyridinium Ylids
A ring-contractive and highly diastereoselective [2,3]-sigmatropic rearrangement occurs when N-methyl-1,2,3,6-tetrahydropyridine is treated with sub-stoichiometric amounts of copper or rhodium salts, in the presence of ethyl diazoacetate, giving ethyl cis-N-methyl-3-ethenyl proline (4).
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| Veröffentlicht in: | Journal of organic chemistry 2003-05, Vol.68 (10), p.4083-4086 |
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| container_end_page | 4086 |
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| container_issue | 10 |
| container_start_page | 4083 |
| container_title | Journal of organic chemistry |
| container_volume | 68 |
| creator | Heath, Peter Roberts, Edward Sweeney, Joseph B Wessel, Hans Peter Workman, James A |
| description | A ring-contractive and highly diastereoselective [2,3]-sigmatropic rearrangement occurs when N-methyl-1,2,3,6-tetrahydropyridine is treated with sub-stoichiometric amounts of copper or rhodium salts, in the presence of ethyl diazoacetate, giving ethyl cis-N-methyl-3-ethenyl proline (4). |
| doi_str_mv | 10.1021/jo034147v |
| format | Article |
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Org. Chem</addtitle><date>2003-05-16</date><risdate>2003</risdate><volume>68</volume><issue>10</issue><spage>4083</spage><epage>4086</epage><pages>4083-4086</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A ring-contractive and highly diastereoselective [2,3]-sigmatropic rearrangement occurs when N-methyl-1,2,3,6-tetrahydropyridine is treated with sub-stoichiometric amounts of copper or rhodium salts, in the presence of ethyl diazoacetate, giving ethyl cis-N-methyl-3-ethenyl proline (4).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12737596</pmid><doi>10.1021/jo034147v</doi><tpages>4</tpages></addata></record> |
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| language | eng |
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| source | ACS Publications |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Copper(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of N-Methyltetrahydropyridinium Ylids |
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