%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