Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles
Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5.0 mol % (S)-p-Tol-BINAP. Th...
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| Format: | Article |
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MDPI AG
2015-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/12/19748 |
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| author | Wen Yang Renshi Luo Dingqiao Yang |
| author_facet | Wen Yang Renshi Luo Dingqiao Yang |
| author_sort | Wen Yang |
| collection | DOAJ |
| description | Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5.0 mol % (S)-p-Tol-BINAP. The effects of various chiral bidentate ligands, catalyst loading, solvent, and temperature on the yield and enantioselectivity were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding trans-ring opened products based on the X-ray structure of product 2i. |
| first_indexed | 2024-12-11T22:39:02Z |
| format | Article |
| id | doaj.art-df93fac7ac4543c4a336b5983d412fc4 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T22:39:02Z |
| publishDate | 2015-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-df93fac7ac4543c4a336b5983d412fc42022-12-22T00:47:52ZengMDPI AGMolecules1420-30492015-11-012012211032112410.3390/molecules201219748molecules201219748Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine NucleophilesWen Yang0Renshi Luo1Dingqiao Yang2Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, ChinaSchool of Pharmaceutical Sciences, Gannan Medical University, Yi Xue Yuan Road, Ganzhou 341000, ChinaKey Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, ChinaIridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5.0 mol % (S)-p-Tol-BINAP. The effects of various chiral bidentate ligands, catalyst loading, solvent, and temperature on the yield and enantioselectivity were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding trans-ring opened products based on the X-ray structure of product 2i.http://www.mdpi.com/1420-3049/20/12/19748iridium catalystasymmetric ring-openingoxabenzonorbornadienechiral bisphosphine ligandN-substituted piperazines |
| spellingShingle | Wen Yang Renshi Luo Dingqiao Yang Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles Molecules iridium catalyst asymmetric ring-opening oxabenzonorbornadiene chiral bisphosphine ligand N-substituted piperazines |
| title | Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles |
| title_full | Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles |
| title_fullStr | Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles |
| title_full_unstemmed | Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles |
| title_short | Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles |
| title_sort | iridium catalyzed asymmetric ring opening of oxabenzonorbornadienes with n substituted piperazine nucleophiles |
| topic | iridium catalyst asymmetric ring-opening oxabenzonorbornadiene chiral bisphosphine ligand N-substituted piperazines |
| url | http://www.mdpi.com/1420-3049/20/12/19748 |
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