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- Title
A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis.
- Authors
Tlais, Sami F.; Clark, Ronald J.; Dudley, Gregory B.
- 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 α-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.
- Subjects
CHELATES; COORDINATION polymers; ASYMMETRIC synthesis; ALCOHOL; CHIRALITY; DIASTEREOISOMERS; ACYCLIC acids; RING formation (Chemistry); CHEMICAL bonds
- Publication
Molecules, 2009, Vol 14, Issue 12, p5216
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules14125216