Functionalized α-oximinoketones as building blocks for the construction of imidazoline-based potential chiral auxiliaries

Rsuini U. Gutiérrez, Araceli Rebollar, Rafael Bautista, Vanessa Pelayo, José Luis Várgas, Mabel M. Montenegro, Carlos Espinoza-Hicks, Francisco Ayala, Pablo M. Bernal, Cuauhtemoc Carrasco, L. Gerardo Zepeda, Francisco Delgado, Joaquín Tamariz

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Functionalized α-oximinoketones with β-alkoxy, β-alkyl, and β-sulfenyl groups were used as efficient synthons for the preparation of chiral 1-acyl-4-imidazolin-2-ones and 1-acylimidazolidin-2-ones. For the preparation of the former heterocycles, α-oximinoketones were transformed into their respective imidazole N-oxides by neutral treatment with a chiral triazine, followed by reaction with acetic or propionic anhydrides to furnish the desired chiral 1-acetyl- or 1-propionyl-4-imidazolin-2-ones in moderate overall yields. Upon palladium hydroxide-catalyzed hydrogenation, these series were converted into their corresponding 1-acylimidazolidin-2-ones in high diastereoisomeric ratios. Thus, these novel chiral 1-acetyl- and 1-propionyl-imidazolidin-2-ones were obtained with a variety of alkyl groups at the C-4 and C-5 positions of the heterocycle, through a three-step methodology, and can be applied as new potential chiral auxiliaries.

Original languageEnglish
Pages (from-to)230-246
Number of pages17
JournalTetrahedron Asymmetry
Volume26
Issue number4
DOIs
StatePublished - 28 Feb 2015

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