A general method for the synthesis of enantiopure 1,5-amino alcohols
A variety of (R)-phenylglycinol-derived oxazolopiperidone lactams 1-14 were converted to linear-chain enantiopure amino diols 15-26 by reduction with LiNH2BH3 in an unprecedented process involving the simultaneous reductive opening of the oxazolidine and lactam rings. Subsequent removal of the pheny...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2016 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2445/98971 |
| Acceso en línea: | https://hdl.handle.net/2445/98971 |
| Access Level: | acceso abierto |
| Palabra clave: | Síntesi orgànica Síntesi asimètrica Reducció química Lactames Organic synthesis Asymmetric synthesis Reduction (Chemistry) Lactams |
| Sumario: | A variety of (R)-phenylglycinol-derived oxazolopiperidone lactams 1-14 were converted to linear-chain enantiopure amino diols 15-26 by reduction with LiNH2BH3 in an unprecedented process involving the simultaneous reductive opening of the oxazolidine and lactam rings. Subsequent removal of the phenylethanol moiety gave enantiopure 5-amino-1-pentanols bearing substituents at the 2-, 3-, 4-, 2,2-, 2,3- 2,4- and 3,4-positions (28-36), which were isolated as their N-Boc derivatives. |
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