One-pot synthesis of alpha,beta-epoxy ketones by palladium-catalyzed epoxidation-oxidation of terminal allylic alcohols

Autor(es)

Singh, Fateh V. ^[1] ; Pena, Jesus M. ^[1] ; Stefani, Helio A. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Tetrahedron Letters; v. 51, n. 13, p. 1671-1673, MAR 31 2010.
• Citações Web of Science: 2

Resumo

Described herein is a one-pot synthesis of a,p-epoxy ketones using a palladium-catalyzed epoxidation-oxidation sequence. Functionalized terminal allylic alcohols are treated with m-CPBA Under mild reaction conditions to obtain the alpha,beta-epoxy ketones. The main benefit of this approach is that the epoxidation of the terminal double bond and the oxidation of the secondary alcohol occured in the same reaction under mild reactions and both electron-donating and electron-withdrawing functionalities are tolerated in the reaction sequence. (C) 2010 Elsevier Ltd. All rights reserved. (AU)

• Processo FAPESP: 07/59404-2 - Reações entre sais de potássio de organotrifluoroboratos e espécies eletrofílicas de telúrio e haletos orgânicos
• Beneficiário: Helio Alexandre Stefani
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 07/51466-9 - Sintese e aplicacao de sais de potassio de 1-bromo-1-trifluoroborato-! e 1-fenil-1-trifluoroborato eteno e 1-bromo-1-n-butitelurio-! 1-fenil-1-n-butitelurio eteno.
• Beneficiário: Fateh Veer Singh
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado