Use of N-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C−C Bond-Forming Reactions with Water

[Image: see text] Indium-promoted coupling reactions between propargyl aldehydes (1) and α-chloropropargylphenyl sulfide are reported. Although water has been shown to accelerate indium metal promoted reactions, the reverse pattern was observed in this series. Use of N-methylformamide (NMF), which h...

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Autores principales: Frimpong, Kwame, Wzorek, Joseph, Lawlor, Claire, Spencer, Katharine, Mitzel, Thomas
Formato: Texto
Lenguaje:English
Publicado: American Chemical Society 2009
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2976581/
https://www.ncbi.nlm.nih.gov/pubmed/19634900
http://dx.doi.org/10.1021/jo900763u
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author Frimpong, Kwame
Wzorek, Joseph
Lawlor, Claire
Spencer, Katharine
Mitzel, Thomas
author_facet Frimpong, Kwame
Wzorek, Joseph
Lawlor, Claire
Spencer, Katharine
Mitzel, Thomas
author_sort Frimpong, Kwame
collection PubMed
description [Image: see text] Indium-promoted coupling reactions between propargyl aldehydes (1) and α-chloropropargylphenyl sulfide are reported. Although water has been shown to accelerate indium metal promoted reactions, the reverse pattern was observed in this series. Use of N-methylformamide (NMF), which has not previously been a solvent known for use in indium-promoted reactions, afforded an acceleration of these Barbier-style reactions compared to water. Indium-promoted reactions in this study also showed excellent regiocontrol and good stereocontrol, allowing for easy entry into the formation of epoxydiyne and enediyne skeletal structures. This paper also describes use of the Barbier Coupled product (2) as a new, and easy, entry into the formation of enediyne and epoxydiyne skeletal structures.
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spelling pubmed-29765812010-11-09 Use of N-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C−C Bond-Forming Reactions with Water Frimpong, Kwame Wzorek, Joseph Lawlor, Claire Spencer, Katharine Mitzel, Thomas J Org Chem [Image: see text] Indium-promoted coupling reactions between propargyl aldehydes (1) and α-chloropropargylphenyl sulfide are reported. Although water has been shown to accelerate indium metal promoted reactions, the reverse pattern was observed in this series. Use of N-methylformamide (NMF), which has not previously been a solvent known for use in indium-promoted reactions, afforded an acceleration of these Barbier-style reactions compared to water. Indium-promoted reactions in this study also showed excellent regiocontrol and good stereocontrol, allowing for easy entry into the formation of epoxydiyne and enediyne skeletal structures. This paper also describes use of the Barbier Coupled product (2) as a new, and easy, entry into the formation of enediyne and epoxydiyne skeletal structures. American Chemical Society 2009-07-27 2009-08-21 /pmc/articles/PMC2976581/ /pubmed/19634900 http://dx.doi.org/10.1021/jo900763u Text en Copyright © 2009 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org.
spellingShingle Frimpong, Kwame
Wzorek, Joseph
Lawlor, Claire
Spencer, Katharine
Mitzel, Thomas
Use of N-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C−C Bond-Forming Reactions with Water
title Use of N-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C−C Bond-Forming Reactions with Water
title_full Use of N-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C−C Bond-Forming Reactions with Water
title_fullStr Use of N-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C−C Bond-Forming Reactions with Water
title_full_unstemmed Use of N-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C−C Bond-Forming Reactions with Water
title_short Use of N-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C−C Bond-Forming Reactions with Water
title_sort use of n-methylformamide as a solvent in indium-promoted barbier reactions en route to enediyne and epoxy diyne formation: comparison of rate and stereoselectivity in c−c bond-forming reactions with water
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2976581/
https://www.ncbi.nlm.nih.gov/pubmed/19634900
http://dx.doi.org/10.1021/jo900763u
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