Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction

[Image: see text] Oxepanes are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. Organocatalytic oxa-conjugate addition reactions promoted by the gem-disubstituent (Thorpe–Ingold) effect stereoselectively provided α,α′-...

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Autores principales: Lanier, Megan L., Kasper, Amanda C., Kim, Hyoungsu, Hong, Jiyong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4018174/
https://www.ncbi.nlm.nih.gov/pubmed/24724535
http://dx.doi.org/10.1021/ol500773w
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author Lanier, Megan L.
Kasper, Amanda C.
Kim, Hyoungsu
Hong, Jiyong
author_facet Lanier, Megan L.
Kasper, Amanda C.
Kim, Hyoungsu
Hong, Jiyong
author_sort Lanier, Megan L.
collection PubMed
description [Image: see text] Oxepanes are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. Organocatalytic oxa-conjugate addition reactions promoted by the gem-disubstituent (Thorpe–Ingold) effect stereoselectively provided α,α′-trans-oxepanes. In addition, the potential of an organocatalytic tandem oxa-conjugate addition/α-oxidation was demonstrated in a rapid generation of molecular complexity. These organocatalytic oxa-conjugate addition reactions would provide powerful tools for the synthesis of natural products that contain highly functionalized oxepanes.
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spelling pubmed-40181742015-04-11 Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction Lanier, Megan L. Kasper, Amanda C. Kim, Hyoungsu Hong, Jiyong Org Lett [Image: see text] Oxepanes are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. Organocatalytic oxa-conjugate addition reactions promoted by the gem-disubstituent (Thorpe–Ingold) effect stereoselectively provided α,α′-trans-oxepanes. In addition, the potential of an organocatalytic tandem oxa-conjugate addition/α-oxidation was demonstrated in a rapid generation of molecular complexity. These organocatalytic oxa-conjugate addition reactions would provide powerful tools for the synthesis of natural products that contain highly functionalized oxepanes. American Chemical Society 2014-04-11 2014-05-02 /pmc/articles/PMC4018174/ /pubmed/24724535 http://dx.doi.org/10.1021/ol500773w Text en Copyright © 2014 American Chemical Society
spellingShingle Lanier, Megan L.
Kasper, Amanda C.
Kim, Hyoungsu
Hong, Jiyong
Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction
title Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction
title_full Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction
title_fullStr Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction
title_full_unstemmed Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction
title_short Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction
title_sort synthesis of α,α′-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4018174/
https://www.ncbi.nlm.nih.gov/pubmed/24724535
http://dx.doi.org/10.1021/ol500773w
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