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A C(1)-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones
A C(1)-symmetric N-heterocyclic carbene (NHC)-catalysed activation of isatin-derived enals under oxidative conditions was achieved. The in situ generated α,β-unsaturated acyl azolium species was efficiently trapped by 1,3-dicarbonyl compounds via a Michael addition/spiroannualtion cascade, deliverin...
| Autores principales: | , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
The Royal Society of Chemistry
2018
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9080099/ https://www.ncbi.nlm.nih.gov/pubmed/35539478 http://dx.doi.org/10.1039/c8ra02009d |
| _version_ | 1784702708332101632 |
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| author | Lin, Jun-Bing Cheng, Xi-Na Tian, Xiao-Dong Xu, Guo-Qiang Luo, Yong-Chun Xu, Peng-Fei |
| author_facet | Lin, Jun-Bing Cheng, Xi-Na Tian, Xiao-Dong Xu, Guo-Qiang Luo, Yong-Chun Xu, Peng-Fei |
| author_sort | Lin, Jun-Bing |
| collection | PubMed |
| description | A C(1)-symmetric N-heterocyclic carbene (NHC)-catalysed activation of isatin-derived enals under oxidative conditions was achieved. The in situ generated α,β-unsaturated acyl azolium species was efficiently trapped by 1,3-dicarbonyl compounds via a Michael addition/spiroannualtion cascade, delivering a series of synthetically important spirooxindole δ-lactones with up to 96% enantioselectivity. |
| format | Online Article Text |
| id | pubmed-9080099 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2018 |
| publisher | The Royal Society of Chemistry |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-90800992022-05-09 A C(1)-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones Lin, Jun-Bing Cheng, Xi-Na Tian, Xiao-Dong Xu, Guo-Qiang Luo, Yong-Chun Xu, Peng-Fei RSC Adv Chemistry A C(1)-symmetric N-heterocyclic carbene (NHC)-catalysed activation of isatin-derived enals under oxidative conditions was achieved. The in situ generated α,β-unsaturated acyl azolium species was efficiently trapped by 1,3-dicarbonyl compounds via a Michael addition/spiroannualtion cascade, delivering a series of synthetically important spirooxindole δ-lactones with up to 96% enantioselectivity. The Royal Society of Chemistry 2018-04-24 /pmc/articles/PMC9080099/ /pubmed/35539478 http://dx.doi.org/10.1039/c8ra02009d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
| spellingShingle | Chemistry Lin, Jun-Bing Cheng, Xi-Na Tian, Xiao-Dong Xu, Guo-Qiang Luo, Yong-Chun Xu, Peng-Fei A C(1)-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones |
| title | A C(1)-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones |
| title_full | A C(1)-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones |
| title_fullStr | A C(1)-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones |
| title_full_unstemmed | A C(1)-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones |
| title_short | A C(1)-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones |
| title_sort | c(1)-symmetric n-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones |
| topic | Chemistry |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9080099/ https://www.ncbi.nlm.nih.gov/pubmed/35539478 http://dx.doi.org/10.1039/c8ra02009d |
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