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Type: Artigo de periódico
Title: Stereoselective synthesis of functionalized trans-2,5-disubstituted tetrahydrofurans
Author: Pilli, RA
Riatto, VB
Vencato, I
Abstract: [GRAPHICS] The addition of the titanium enolates of N-acetyl, N-propionyl, and N-bromoacetyl (R)-oxazolidin-2-ones to gamma-lactol 2, derived from (S)-glutamic acid, afforded trans- and cis-2,5-disubstituted tetrahydrofurans (trans/cis ratio: R = H, 2:1; R = Me, 8:1; R = Br, 10:1) after desilylation with aqueous HF/CH3CN, Chromatographic separation and LiBH4 reduction allowed the efficient preparation of the corresponding trans-2,5-disubstituted tetrahydrofuran diols and the recovery of the chiral auxiliary.
Country: EUA
Editor: Amer Chemical Soc
Citation: Organic Letters. Amer Chemical Soc, v. 2, n. 1, n. 53, n. 56, 2000.
Rights: fechado
Identifier DOI: 10.1021/ol991194u
Date Issue: 2000
Appears in Collections:Unicamp - Artigos e Outros Documentos

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