Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization
The utilization of 6,6-dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one made from an unsymmetrical 4,4-dimethylcyclohexane-1,3-dione in iridium-catalyzed allylic enolization involving keto-enol isomerization is accomplished under mild conditions. The chemoselectivity, regioselectivity, and enanti...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/20/6981 |
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| author | Xiao-Lin Wang Ji-Teng Chen Sheng-Cai Zheng Xiao-Ming Zhao |
| author_facet | Xiao-Lin Wang Ji-Teng Chen Sheng-Cai Zheng Xiao-Ming Zhao |
| author_sort | Xiao-Lin Wang |
| collection | DOAJ |
| description | The utilization of 6,6-dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one made from an unsymmetrical 4,4-dimethylcyclohexane-1,3-dione in iridium-catalyzed allylic enolization involving keto-enol isomerization is accomplished under mild conditions. The chemoselectivity, regioselectivity, and enantioselectivity are facilitated by the quaternary carbon and adjusting the reaction conditions. This method provides the substituted 2-(but-3-en-2-yl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-ones in good to high yields with high level of chemo-, regio-, and enantioselectivities. The chiral carbon-fluorine bond formation is induced by an adjacent chiral carbon center of the allylated 3-hydroxy-6,6-dimethylcyclohex-2-en-1-one, as well. |
| first_indexed | 2024-03-09T19:42:05Z |
| format | Article |
| id | doaj.art-1691ba6d53424c2581bef7f912527164 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T19:42:05Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1691ba6d53424c2581bef7f9125271642023-11-24T01:35:00ZengMDPI AGMolecules1420-30492022-10-012720698110.3390/molecules27206981Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol IsomerizationXiao-Lin Wang0Ji-Teng Chen1Sheng-Cai Zheng2Xiao-Ming Zhao3School of Chemical Technology and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, ChinaSchool of Chemical Technology and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, ChinaSchool of Chemical Technology and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, ChinaSchool of Chemical Technology and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, ChinaThe utilization of 6,6-dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one made from an unsymmetrical 4,4-dimethylcyclohexane-1,3-dione in iridium-catalyzed allylic enolization involving keto-enol isomerization is accomplished under mild conditions. The chemoselectivity, regioselectivity, and enantioselectivity are facilitated by the quaternary carbon and adjusting the reaction conditions. This method provides the substituted 2-(but-3-en-2-yl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-ones in good to high yields with high level of chemo-, regio-, and enantioselectivities. The chiral carbon-fluorine bond formation is induced by an adjacent chiral carbon center of the allylated 3-hydroxy-6,6-dimethylcyclohex-2-en-1-one, as well.https://www.mdpi.com/1420-3049/27/20/6981enolizationchemoselectivityregioselectivityenantioselectivityfluorination |
| spellingShingle | Xiao-Lin Wang Ji-Teng Chen Sheng-Cai Zheng Xiao-Ming Zhao Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization Molecules enolization chemoselectivity regioselectivity enantioselectivity fluorination |
| title | Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization |
| title_full | Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization |
| title_fullStr | Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization |
| title_full_unstemmed | Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization |
| title_short | Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization |
| title_sort | ir catalyzed chemo regio and enantioselective allylic enolization of 6 6 dimethyl 3 trimethylsilyl oxy cyclohex 2 en 1 one involving keto enol isomerization |
| topic | enolization chemoselectivity regioselectivity enantioselectivity fluorination |
| url | https://www.mdpi.com/1420-3049/27/20/6981 |
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