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

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

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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)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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