A striking exception to the chelate model for acyclic diastereocontrol: efficient access to a versatile propargyl alcohol for chemical synthesis.
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.
Tlais
Sami F
SF
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA. stlais@chem.fsu.edu
Clark
Ronald J
RJ
Dudley
Gregory B
GB
D000480:Alkynes / Q000737:chemistry*; D002614:Chelating Agents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D020005:Propanols / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D000480:Alkynes; D002614:Chelating Agents; D020005:Propanols; C028255:propargyl alcohol