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Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters
In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon ce...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778419/ https://www.ncbi.nlm.nih.gov/pubmed/24062852 http://dx.doi.org/10.3762/bjoc.9.216 |
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author | Yan, Lin Han, Zhiqiang Zhu, Bo Yang, Caiyun Tan, Choon-Hong Jiang, Zhiyong |
author_facet | Yan, Lin Han, Zhiqiang Zhu, Bo Yang, Caiyun Tan, Choon-Hong Jiang, Zhiyong |
author_sort | Yan, Lin |
collection | PubMed |
description | In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr). |
format | Online Article Text |
id | pubmed-3778419 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-37784192013-09-23 Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters Yan, Lin Han, Zhiqiang Zhu, Bo Yang, Caiyun Tan, Choon-Hong Jiang, Zhiyong Beilstein J Org Chem Full Research Paper In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr). Beilstein-Institut 2013-09-11 /pmc/articles/PMC3778419/ /pubmed/24062852 http://dx.doi.org/10.3762/bjoc.9.216 Text en Copyright © 2013, Yan et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Yan, Lin Han, Zhiqiang Zhu, Bo Yang, Caiyun Tan, Choon-Hong Jiang, Zhiyong Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
title | Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
title_full | Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
title_fullStr | Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
title_full_unstemmed | Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
title_short | Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters |
title_sort | asymmetric allylic alkylation of morita–baylis–hillman carbonates with α-fluoro-β-keto esters |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778419/ https://www.ncbi.nlm.nih.gov/pubmed/24062852 http://dx.doi.org/10.3762/bjoc.9.216 |
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