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Open AccessArticle

A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis

Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA
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Molecules 2009, 14(12), 5216-5222; https://doi.org/10.3390/molecules14125216
Received: 26 October 2009 / Revised: 17 November 2009 / Accepted: 30 November 2009 / Published: 15 December 2009
(This article belongs to the Special Issue Asymmetric 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 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. View Full-Text
Keywords: pantolactone; synthesis; Felkin–Anh; acyclic diastereocontrol; chiral building block pantolactone; synthesis; Felkin–Anh; acyclic diastereocontrol; chiral building block
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Tlais, S.F.; Clark, R.J.; Dudley, G.B. A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis. Molecules 2009, 14, 5216-5222.

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