Synthesis of enantiomerically pure constrained gamma-hydroxy-alfa-amino acids by directed hydroxylation
Efficient synthetic routes to enantiomerically pure (1R,3R,6R)- and (1S,3S,6S)-1-amino-3-hydroxy-6-phenylcyclohexane-1- carboxylic acids have been developed. The key step is a directed hydroxylation through an iodo-initiated O-functionalization reaction of methyl (1S,6R)- and (1R,6S)-1-aminocarbonyl...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 1997 |
| País: | España |
| Institución: | Universidad de La Rioja (UR) |
| Repositorio: | RIUR. Repositorio Institucional de la Universidad de La Rioja |
| OAI Identifier: | oai:portal.dialnet.es:doc/5bbc68feb750603269e81321 |
| Acceso en línea: | https://investigacion.unirioja.es/documentos/5bbc68feb750603269e81321 |
| Access Level: | acceso abierto |
| Sumario: | Efficient synthetic routes to enantiomerically pure (1R,3R,6R)- and (1S,3S,6S)-1-amino-3-hydroxy-6-phenylcyclohexane-1- carboxylic acids have been developed. The key step is a directed hydroxylation through an iodo-initiated O-functionalization reaction of methyl (1S,6R)- and (1R,6S)-1-aminocarbonyl-6-phenyl-3-cyclohexene-1- carboxylates, which can easily be obtained from the asymmetric Diels-Alder reactions of 1,3-butadiene with the (E)-2-cyanocinnamates of (S)-ethyl lactate and (R)-pantolactone, respectively. |
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