Lipase catalysed kinetic resolution of racemic 1,2-diols containing a chiral quaternary center
Optically active 1,2-diols are valuable buildings blocks in organic synthesis. In the present paper, a set of racemic 1,2-diols with an ester functional group are prepared, starting from -ketoesters in a three-step procedure with moderate yields. The racemic 1,2-diols, containing a chiral quaternary...
| Autor: | |
|---|---|
| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2018 |
| País: | España |
| Recursos: | Universidad de Sevilla (US) |
| Repositorio: | idUS. Depósito de Investigación de la Universidad de Sevilla |
| OAI Identifier: | oai:idus.us.es:11441/77844 |
| Acesso em linha: | https://hdl.handle.net/11441/77844 https://doi.org/10.3390/molecules23071585 |
| Access Level: | acceso abierto |
| Palavra-chave: | Biocatalysis Lipases Kinetic resolution 1,2-diols |
| Resumo: | Optically active 1,2-diols are valuable buildings blocks in organic synthesis. In the present paper, a set of racemic 1,2-diols with an ester functional group are prepared, starting from -ketoesters in a three-step procedure with moderate yields. The racemic 1,2-diols, containing a chiral quaternary center in their structure, are subjected to selective acylation in order to perform their kinetic resolution catalysed by a set of commercially available lipases. Under optimized reaction conditions, good conversions and enantioselectivities are achieved by using the lipase PSL-C from Pseudomonas cepacia in tert-butyl methyl ether. This biocatalyst could be reused up to five times without losing its properties. |
|---|