Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides

A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were fou...

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Autores principales: Xu, Lingjun, Han, Shuwen, Yan, Linjie, Wang, Haifeng, Peng, Haihui, Chen, Fener
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5815282/
https://www.ncbi.nlm.nih.gov/pubmed/29507636
http://dx.doi.org/10.3762/bjoc.14.19
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author Xu, Lingjun
Han, Shuwen
Yan, Linjie
Wang, Haifeng
Peng, Haihui
Chen, Fener
author_facet Xu, Lingjun
Han, Shuwen
Yan, Linjie
Wang, Haifeng
Peng, Haihui
Chen, Fener
author_sort Xu, Lingjun
collection PubMed
description A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.
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spelling pubmed-58152822018-03-05 Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides Xu, Lingjun Han, Shuwen Yan, Linjie Wang, Haifeng Peng, Haihui Chen, Fener Beilstein J Org Chem Full Research Paper A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB. Beilstein-Institut 2018-01-31 /pmc/articles/PMC5815282/ /pubmed/29507636 http://dx.doi.org/10.3762/bjoc.14.19 Text en Copyright © 2018, Xu et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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
Xu, Lingjun
Han, Shuwen
Yan, Linjie
Wang, Haifeng
Peng, Haihui
Chen, Fener
Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
title Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
title_full Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
title_fullStr Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
title_full_unstemmed Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
title_short Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
title_sort novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5815282/
https://www.ncbi.nlm.nih.gov/pubmed/29507636
http://dx.doi.org/10.3762/bjoc.14.19
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