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 α-alkoxy-aldehyde 7, in which unusual Felkin selectivity is observed, despite the potential for chelation cont...

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Detalles Bibliográficos
Autores principales: Tlais, Sami F., Clark, Ronald J., Dudley, Gregory B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254915/
https://www.ncbi.nlm.nih.gov/pubmed/20032887
http://dx.doi.org/10.3390/molecules14125216
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author Tlais, Sami F.
Clark, Ronald J.
Dudley, Gregory B.
author_facet Tlais, Sami F.
Clark, Ronald J.
Dudley, Gregory B.
author_sort Tlais, Sami F.
collection PubMed
description 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.
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spelling pubmed-62549152018-11-30 A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis Tlais, Sami F. Clark, Ronald J. Dudley, Gregory B. Molecules Article 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. Molecular Diversity Preservation International 2009-12-15 /pmc/articles/PMC6254915/ /pubmed/20032887 http://dx.doi.org/10.3390/molecules14125216 Text en © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Tlais, Sami F.
Clark, Ronald J.
Dudley, Gregory B.
A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
title A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
title_full A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
title_fullStr A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
title_full_unstemmed A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
title_short A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
title_sort striking exception to the chelate model for acyclic diastereocontrol: efficient access to a versatile propargyl alcohol for chemical synthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254915/
https://www.ncbi.nlm.nih.gov/pubmed/20032887
http://dx.doi.org/10.3390/molecules14125216
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