Ruthenium-Porphyrin-Catalyzed [4 + 2] Cycloaddition of α,β-Unsaturated Imines and Aldehydes
A new efficient synthetic route to unsymmetrically substituted dihydropyridine scaffolds via dehydrative [4 + 2] cycloaddition of N-tosylated α,β-unsaturated imines with aldehydes has been developed. This transformation is enabled by (i) the remarkable catalytic ability of the cationic Ru(IV) porph...
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| Veröffentlicht in: | Organic letters 2015-11, Vol.17 (21), p.5284-5287 |
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| container_issue | 21 |
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| container_title | Organic letters |
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| creator | Maeda, Kazuki Terada, Takuma Iwamoto, Takahiro Kurahashi, Takuya Matsubara, Seijiro |
| description | A new efficient synthetic route to unsymmetrically substituted dihydropyridine scaffolds via dehydrative [4 + 2] cycloaddition of N-tosylated α,β-unsaturated imines with aldehydes has been developed. This transformation is enabled by (i) the remarkable catalytic ability of the cationic Ru(IV) porphyrin complex to activate both the imino and carbonyl groups and (ii) the hydrophobic nature of the porphyrin ligand, which helps realize robust Lewis acidity in the dehydrative cycloaddition. |
| doi_str_mv | 10.1021/acs.orglett.5b02654 |
| format | Article |
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Lett</addtitle><date>2015-11-06</date><risdate>2015</risdate><volume>17</volume><issue>21</issue><spage>5284</spage><epage>5287</epage><pages>5284-5287</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A new efficient synthetic route to unsymmetrically substituted dihydropyridine scaffolds via dehydrative [4 + 2] cycloaddition of N-tosylated α,β-unsaturated imines with aldehydes has been developed. This transformation is enabled by (i) the remarkable catalytic ability of the cationic Ru(IV) porphyrin complex to activate both the imino and carbonyl groups and (ii) the hydrophobic nature of the porphyrin ligand, which helps realize robust Lewis acidity in the dehydrative cycloaddition.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26492441</pmid><doi>10.1021/acs.orglett.5b02654</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2015-11, Vol.17 (21), p.5284-5287 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Aldehydes - chemistry Catalysis Cycloaddition Reaction Dihydropyridines - chemical synthesis Dihydropyridines - chemistry Imines - chemistry Lewis Acids - chemistry Metalloporphyrins - chemistry Molecular Structure Ruthenium - chemistry |
| title | Ruthenium-Porphyrin-Catalyzed [4 + 2] Cycloaddition of α,β-Unsaturated Imines and Aldehydes |
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