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A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst
An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported. Both enantiomers of the Michael adducts can be obtained in high enantioselectivity and good yield merely by changing th...
| Autores principales: | , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Royal Society of Chemistry
2020
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7444369/ https://www.ncbi.nlm.nih.gov/pubmed/32874501 http://dx.doi.org/10.1039/d0sc01729a |
| _version_ | 1783573792765771776 |
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| author | Hayama, Noboru Kobayashi, Yusuke Sekimoto, Eriko Miyazaki, Anna Inamoto, Kiyofumi Kimachi, Tetsutaro Takemoto, Yoshiji |
| author_facet | Hayama, Noboru Kobayashi, Yusuke Sekimoto, Eriko Miyazaki, Anna Inamoto, Kiyofumi Kimachi, Tetsutaro Takemoto, Yoshiji |
| author_sort | Hayama, Noboru |
| collection | PubMed |
| description | An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported. Both enantiomers of the Michael adducts can be obtained in high enantioselectivity and good yield merely by changing the solvent. The origin of the chirality switch in the products was examined in each solvent via spectroscopic analyses. |
| format | Online Article Text |
| id | pubmed-7444369 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2020 |
| publisher | Royal Society of Chemistry |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-74443692020-08-31 A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst Hayama, Noboru Kobayashi, Yusuke Sekimoto, Eriko Miyazaki, Anna Inamoto, Kiyofumi Kimachi, Tetsutaro Takemoto, Yoshiji Chem Sci Chemistry An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported. Both enantiomers of the Michael adducts can be obtained in high enantioselectivity and good yield merely by changing the solvent. The origin of the chirality switch in the products was examined in each solvent via spectroscopic analyses. Royal Society of Chemistry 2020-05-14 /pmc/articles/PMC7444369/ /pubmed/32874501 http://dx.doi.org/10.1039/d0sc01729a Text en This journal is © The Royal Society of Chemistry 2020 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0) |
| spellingShingle | Chemistry Hayama, Noboru Kobayashi, Yusuke Sekimoto, Eriko Miyazaki, Anna Inamoto, Kiyofumi Kimachi, Tetsutaro Takemoto, Yoshiji A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst |
| title | A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst
|
| title_full | A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst
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| title_fullStr | A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst
|
| title_full_unstemmed | A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst
|
| title_short | A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst
|
| title_sort | solvent-dependent chirality-switchable thia-michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst |
| topic | Chemistry |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7444369/ https://www.ncbi.nlm.nih.gov/pubmed/32874501 http://dx.doi.org/10.1039/d0sc01729a |
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