Regio- and enantioselective bioreduction of methyleneketoesters using both polymeric resin and cellulose matrix

Autor:	J. Augusto R. Rodrigues, Michel R. B. Chaves, Paulo J. S. Moran
Rok vydání:	2013
Předmět:	Filter paper Process Chemistry and Technology Enantioselective synthesis Substrate (chemistry) Bioengineering Biochemistry Catalysis Matrix (chemical analysis) chemistry.chemical_compound Adsorption chemistry Yield (chemistry) Organic chemistry Stereoselectivity Cellulose
Zdroj:	Journal of Molecular Catalysis B: Enzymatic. 98:73-77
ISSN:	1381-1177
DOI:	10.1016/j.molcatb.2013.09.018
Popis:	Methyleneketoesters were prepared in >90% yield by performing an IBX oxidation of Morita–Baylis–Hillman adducts. A methodology was developed to achieve methyl 3-aryl-3-keto-2-methylenepropanoate reduction using a screening of yeast strains in three different reaction procedures to obtain products with both high yield and diastereoselectivity. The reactions conducted in water provided inferior yields (50%) for substrates 2b–c. Employing Amberlite® XAD7HP which was a substrate reservoir that also immediately extracted the products from the reaction medium after their formation, syn-4a–c and anti-4a–c were isolated in 60–70% yield, with high stereoselectivity (98–99% ee). The best results were obtained using substrates adsorbed on filter paper which provided products yields above 70%, a 99% ee and a diastereomoeric ratio (syn-4: anti-4) 9:1. Cellulose matrix has excellent potential to be successfully employed in general biocatalytic reactions.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ac5e9056aec865b69c77f0d9e949d9f5 https://doi.org/10.1016/j.molcatb.2013.09.018 Zobrazit plný text záznamu Full Text from ScienceDirect