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Updated: Jun 17, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
A striking exception to the chelate model for acyclic diastereocontrol: efficient access to a versatile propargyl
Sami F Tlais1, Ronald J Clark, Gregory B Dudley
1Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA. stlais@chem.fsu.edu
Abstract:
The four-step, asymmetric synthesis of a chiral propargyl alcohol 1 from (R)-pantolactone is described. A key feature of the synthesis is a diastereoselective acetylide addition to a chiral alpha-alkoxy-aldehyde 7, in which unusual Felkin selectivity is observed, despite the potential for chelation control. Crystalline propargyl alcohol 1 is valuable for complex molecule synthesis, and is easy to prepare in multi-gram quantities and high diastereomeric purity.
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