期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 352, 期 10, 页码 1657-1661出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000353
关键词
alcohol dehydrogenases; bromohydrins; epoxides; medium engineering; one-pot reaction; prolinol
资金
- European Union [E07D402519AR]
- Universidad de Oviedo
- Spanish Ministerio de Ciencia e Innovacion (MICINN)
- MICINN [CTQ2007-61126]
- Spanish Ministerio de Asuntos Exteriores y de Cooperacion
- PCI Iberoamerica MAEC-AECID [A/8856/07]
Different enantiopure terminal epoxides or bromohydrins have chemoselectively been synthesised in one-pot starting from the corresponding a-bromo ketones through alcohol dehydrogenase (ADH)-catalysed processes adding an organic co-solvent and tuning appropriately the medium pH and the temperature. Thus, at neutral pH enantiopure bromohydrins were obtained while using basic conditions (pH 9.5-10) epoxides were isolated as the main product. Furthermore, by simple selection of the biocatalyst, chemo- and stereodivergent transformations were achieved to obtain, e.g., enantiopure prolinol or piperidin-3-ol.
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