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Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone
Two catalytic asymmetric vinylogous aldol-type reactions of aldehydes with allyl phosphonate and allyl sulfone have been uncovered in good to high yields for the first time. The bulky ligand—(R)-DTBM-SEGPHOS—was found to be the key to perfectly control both regio- and enantioselectivities. Transform...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Elsevier
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6443912/ https://www.ncbi.nlm.nih.gov/pubmed/30928697 http://dx.doi.org/10.1016/j.isci.2019.03.010 |
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author | Yue, Wen-Jun Zhang, Cheng-Yuan Yin, Liang |
author_facet | Yue, Wen-Jun Zhang, Cheng-Yuan Yin, Liang |
author_sort | Yue, Wen-Jun |
collection | PubMed |
description | Two catalytic asymmetric vinylogous aldol-type reactions of aldehydes with allyl phosphonate and allyl sulfone have been uncovered in good to high yields for the first time. The bulky ligand—(R)-DTBM-SEGPHOS—was found to be the key to perfectly control both regio- and enantioselectivities. Transformations of the vinylogous products (including Horner-Wadsworth-Emmons and Julia olefinations) were successfully realized by virtue of the phosphonate and sulfone moieties. Moreover, the present methodology was successfully applied in the asymmetric synthesis of natural products. |
format | Online Article Text |
id | pubmed-6443912 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Elsevier |
record_format | MEDLINE/PubMed |
spelling | pubmed-64439122019-04-11 Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone Yue, Wen-Jun Zhang, Cheng-Yuan Yin, Liang iScience Article Two catalytic asymmetric vinylogous aldol-type reactions of aldehydes with allyl phosphonate and allyl sulfone have been uncovered in good to high yields for the first time. The bulky ligand—(R)-DTBM-SEGPHOS—was found to be the key to perfectly control both regio- and enantioselectivities. Transformations of the vinylogous products (including Horner-Wadsworth-Emmons and Julia olefinations) were successfully realized by virtue of the phosphonate and sulfone moieties. Moreover, the present methodology was successfully applied in the asymmetric synthesis of natural products. Elsevier 2019-03-16 /pmc/articles/PMC6443912/ /pubmed/30928697 http://dx.doi.org/10.1016/j.isci.2019.03.010 Text en © 2019 The Author(s) http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Article Yue, Wen-Jun Zhang, Cheng-Yuan Yin, Liang Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone |
title | Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone |
title_full | Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone |
title_fullStr | Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone |
title_full_unstemmed | Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone |
title_short | Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone |
title_sort | asymmetric vinylogous aldol-type reactions of aldehydes with allyl phosphonate and sulfone |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6443912/ https://www.ncbi.nlm.nih.gov/pubmed/30928697 http://dx.doi.org/10.1016/j.isci.2019.03.010 |
work_keys_str_mv | AT yuewenjun asymmetricvinylogousaldoltypereactionsofaldehydeswithallylphosphonateandsulfone AT zhangchengyuan asymmetricvinylogousaldoltypereactionsofaldehydeswithallylphosphonateandsulfone AT yinliang asymmetricvinylogousaldoltypereactionsofaldehydeswithallylphosphonateandsulfone |