Cargando…
Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions
Four catalysts based on new amides of chiral 1,2-diamines and 2-sulfobenzoic acid have been developed. The alkali-metal salts of these betaine-like amides are able to form imines with enones, which are activated by Lewis acid interaction for nucleophilic attack by 4-hydroxycoumarin. The addition of...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2013
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566766/ https://www.ncbi.nlm.nih.gov/pubmed/23400419 http://dx.doi.org/10.3762/bjoc.9.18 |
_version_ | 1782258600101543936 |
---|---|
author | Leven, Matthias Neudörfl, Jörg M Goldfuss, Bernd |
author_facet | Leven, Matthias Neudörfl, Jörg M Goldfuss, Bernd |
author_sort | Leven, Matthias |
collection | PubMed |
description | Four catalysts based on new amides of chiral 1,2-diamines and 2-sulfobenzoic acid have been developed. The alkali-metal salts of these betaine-like amides are able to form imines with enones, which are activated by Lewis acid interaction for nucleophilic attack by 4-hydroxycoumarin. The addition of 4-hydroxycoumarin to enones gives ee’s up to 83% and almost quantitative yields in many cases. This novel type of catalysis provides an effective alternative to conventional primary amino catalysis were strong acid additives are essential components. |
format | Online Article Text |
id | pubmed-3566766 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-35667662013-02-11 Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions Leven, Matthias Neudörfl, Jörg M Goldfuss, Bernd Beilstein J Org Chem Full Research Paper Four catalysts based on new amides of chiral 1,2-diamines and 2-sulfobenzoic acid have been developed. The alkali-metal salts of these betaine-like amides are able to form imines with enones, which are activated by Lewis acid interaction for nucleophilic attack by 4-hydroxycoumarin. The addition of 4-hydroxycoumarin to enones gives ee’s up to 83% and almost quantitative yields in many cases. This novel type of catalysis provides an effective alternative to conventional primary amino catalysis were strong acid additives are essential components. Beilstein-Institut 2013-01-23 /pmc/articles/PMC3566766/ /pubmed/23400419 http://dx.doi.org/10.3762/bjoc.9.18 Text en Copyright © 2013, Leven 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 Leven, Matthias Neudörfl, Jörg M Goldfuss, Bernd Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions |
title | Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions |
title_full | Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions |
title_fullStr | Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions |
title_full_unstemmed | Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions |
title_short | Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions |
title_sort | metal-mediated aminocatalysis provides mild conditions: enantioselective michael addition mediated by primary amino catalysts and alkali-metal ions |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566766/ https://www.ncbi.nlm.nih.gov/pubmed/23400419 http://dx.doi.org/10.3762/bjoc.9.18 |
work_keys_str_mv | AT levenmatthias metalmediatedaminocatalysisprovidesmildconditionsenantioselectivemichaeladditionmediatedbyprimaryaminocatalystsandalkalimetalions AT neudorfljorgm metalmediatedaminocatalysisprovidesmildconditionsenantioselectivemichaeladditionmediatedbyprimaryaminocatalystsandalkalimetalions AT goldfussbernd metalmediatedaminocatalysisprovidesmildconditionsenantioselectivemichaeladditionmediatedbyprimaryaminocatalystsandalkalimetalions |