%0 Journal Article %A Pilli, Ronaldo A. %A Riatto, Valéria B. %A Vencato, Ivo %D 1999 %T Stereoselective Synthesis of Functionalized trans-2,5-Disubstituted Tetrahydrofurans %U https://acs.figshare.com/articles/journal_contribution/Stereoselective_Synthesis_of_Functionalized_i_trans_i_-2_5-Disubstituted_Tetrahydrofurans/3761358 %R 10.1021/ol991194u.s002 %2 https://ndownloader.figshare.com/files/5868651 %K ci %K Chromatographic separation %K Stereoselective Synthesis %K HF %K CN %K tetrahydrofuran %K titanium enolates %K tran %K disubstituted %K LiBH 4 reduction %X The addition of the titanium enolates of N-acetyl, N-propionyl, and N-bromoacetyl (R)-oxazolidin-2-ones to γ-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. %I ACS Publications