Coumarins from Free ortho-Hydroxy Cinnamates by Heck-Matsuda Arylations: A Scalable Total Synthesis of (R)‑Tolterodine
Free ortho-hydroxy cinnamate ester derivatives are evaluated in the synthesis of structurally diverse 4-aryl-coumarins via a tandem Heck-Matsuda cyclization reaction. Free phenolic groups were considered incompatible with such a reaction, which usually provide the corresponding diazo dyes. A concise...
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| Veröffentlicht in: | Organic letters 2012-12, Vol.14 (23), p.6036-6039 |
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| container_title | Organic letters |
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| creator | Barancelli, Daniela A Salles, Airton G Taylor, Jason G Correia, Carlos Roque D |
| description | Free ortho-hydroxy cinnamate ester derivatives are evaluated in the synthesis of structurally diverse 4-aryl-coumarins via a tandem Heck-Matsuda cyclization reaction. Free phenolic groups were considered incompatible with such a reaction, which usually provide the corresponding diazo dyes. A concise and scalable route employing a ligand-free, Pd-catalyzed Heck-Matsuda arylation under aerobic conditions for the preparation of (R)-Tolterodine in high overall yield and ee is also presented. |
| doi_str_mv | 10.1021/ol302923f |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2012-12, Vol.14 (23), p.6036-6039 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1237514236 |
| source | MEDLINE; ACS Publications |
| subjects | Benzhydryl Compounds - chemical synthesis Benzhydryl Compounds - chemistry Catalysis Cinnamates - chemistry Coumarins - chemical synthesis Coumarins - chemistry Cresols - chemical synthesis Cresols - chemistry Cyclization Esters Molecular Structure Palladium - chemistry Phenylpropanolamine - chemical synthesis Phenylpropanolamine - chemistry Stereoisomerism Tolterodine Tartrate |
| title | Coumarins from Free ortho-Hydroxy Cinnamates by Heck-Matsuda Arylations: A Scalable Total Synthesis of (R)‑Tolterodine |
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