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

doi:10.3390/molecules14125216

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Molecules 2009, 14(12), 5216-5222; doi:10.3390/molecules14125216

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

Sami F. Tlais, Ronald J. Clark and Gregory B. Dudley*

Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA

* Author to whom correspondence should be addressed.

Received: 26 October 2009; in revised form: 17 November 2009 / Accepted: 30 November 2009 / Published: 15 December 2009

(This article belongs to the Special Issue Asymmetric Synthesis)

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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.

Keywords: pantolactone; synthesis; Felkin–Anh; acyclic diastereocontrol; chiral building block

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MDPI and ACS Style

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.

AMA Style

Tlais SF, Clark RJ, Dudley GB. A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis. Molecules. 2009; 14(12):5216-5222.

Chicago/Turabian Style

Tlais, Sami F.; Clark, Ronald J.; Dudley, Gregory B. 2009. "A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis." Molecules 14, no. 12: 5216-5222.

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