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Type: Artigo de periódico
Title: Diastereoselective Reduction Of E And Z α-alkoxyimino-β-ketoesters By Sodium Borohydride
Author: Correa Jr. I.R.
Moran P.J.S.
Abstract: The reduction of (Z)-α-alkoxyimino-β-ketoesters, R1COC(= NOR3)CO2R2 (R1 = Me, Et, MeOCH2, Ph; R2 = Me, Et, PhCH2; R3 = Me, PhCH2) with NaBH4/THF-MeOH at 0 °C gave the corresponding (Z)-α- alkoxyimino-β-hydroxyesters in 72-85% yield while the E isomers gave a mixture of corresponding (Z)- and (E)-2-alkoxyimino-1,3-diols in 71-85% yield. The (E)-α-alkoxyimino-β-hydroxyesters were obtained in 71-85% yield when the reaction temperature was -72 °C. The 13C-NMR and IR spectra of (E)- and (Z)-α-oxyimino-β-ketoesters and (E)- and (Z)-α-alkoxyimino-β- ketoesters, were used for determination of E/Z configuration. The C(γ) signals in 13C-NMR of Z are shifted to higher field and the IR spectra of E isomers show a splitting of C = O ester band.
Rights: fechado
Identifier DOI: 10.1016/S0040-4020(99)00897-2
Date Issue: 1999
Appears in Collections:Unicamp - Artigos e Outros Documentos

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