Chiral α,ω-dioxy-carbanions from 1,3-propanediol and 1,4-butanediol by sparteine-assisted deprotonation. Enantioselective synthesis of 1,3- and 1,4-diols, (R)-pantolactone, and a cyclopropane.

Stereoselective generation of 1,3- and 1

Stereoselective generation of 1,3- and 1,4-dioxy-substituted carbanions by sparteine-assisted deprotonation of chiral precursors: Substrate or reagent control in the synthesis of α,γ- and α,δ-diols

✍ Hartmut Ahrens; Mario Paetow; Dieter Hoppe 📂 Article 📅 1992 🏛 Elsevier Science 🌐 French ⚖ 194 KB

The deprotonation of a dicarbamate, derived from (S)-butane-13-diol, by sec-butyllithium takes an highly diastereoselective, but opposite, direction in the presence of (-)-sparteine and of tetramethylethylenediamine (TMEDA ), respectively. The (S)-pentane-1,4-diol derivative shows the same stereoche