Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
The synthesis of a series of chiral secondary alcohols derived from (R)-carvone, and the stereochemical outcome of their reaction with (±)-ibuprofen, is reported. The racemic drug was transformed into the corresponding diastereomeric esters mediated by DCC/DMAP, affording up to 5.7:1 diastereomeric...
| Autores: | , , |
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| Tipo de documento: | artigo |
| Estado: | Versão publicada |
| Data de publicação: | 2010 |
| País: | Argentina |
| Recursos: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositório: | CONICET Digital (CONICET) |
| Idioma: | inglês |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/152281 |
| Acesso em linha: | http://hdl.handle.net/11336/152281 |
| Access Level: | Acceso aberto |
| Palavra-chave: | CARVONE CHIRAL AUXILIARIES CHIRAL SECONDARY ALCOHOLS IBUPROFEN STEGLICH ESTERIFCATION https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Resumo: | The synthesis of a series of chiral secondary alcohols derived from (R)-carvone, and the stereochemical outcome of their reaction with (±)-ibuprofen, is reported. The racemic drug was transformed into the corresponding diastereomeric esters mediated by DCC/DMAP, affording up to 5.7:1 diastereomeric ratios of the esters derived from either (S)-or (R)-ibuprofen, depending on the type of chiral auxiliary employed. |
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