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

Autor(es)

Chaves, Michel R. B. ^[1] ; Moran, Paulo J. S. ^[1] ; Rodrigues, J. Augusto R. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, BR-13084971 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC; v. 98, p. 73-77, DEC 30 2013.
• Citações Web of Science: 4

Resumo

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 (R) 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. (C) 2013 Elsevier B.V. All rights reserved. (AU)

• Processo FAPESP: 11/51861-0 - Biocatálise e química orgânica
• Beneficiário: José Augusto Rosário Rodrigues
• Modalidade de apoio: Auxílio à Pesquisa - Regular