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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...

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Detalles Bibliográficos
Autores principales: Yan, Lin, Han, Zhiqiang, Zhu, Bo, Yang, Caiyun, Tan, Choon-Hong, Jiang, Zhiyong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
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).
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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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