Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the pres...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2009-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.5.53 |
| _version_ | 1818445131748999168 |
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| author | Dingqiao Yang Ping Hu Yuhua Long Yujuan Wu Heping Zeng Hui Wang Xiongjun Zuo |
| author_facet | Dingqiao Yang Ping Hu Yuhua Long Yujuan Wu Heping Zeng Hui Wang Xiongjun Zuo |
| author_sort | Dingqiao Yang |
| collection | DOAJ |
| description | Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration of 3f was confirmed by X-ray crystallography. |
| first_indexed | 2024-12-14T19:26:57Z |
| format | Article |
| id | doaj.art-dabb5789e5974228b5a9a76adaf2afdb |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T19:26:57Z |
| publishDate | 2009-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-dabb5789e5974228b5a9a76adaf2afdb2022-12-21T22:50:11ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972009-10-01515310.3762/bjoc.5.531860-5397-5-53Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophilesDingqiao Yang0Ping Hu1Yuhua Long2Yujuan Wu3Heping Zeng4Hui Wang5Xiongjun Zuo6School of Chemistry and Environment, South China Normal University, Guangzhou 510006, People’s Republic of China, Fax: (+86)-20-39310187; Phone: (+86)-20-85210087School of Chemistry and Environment, South China Normal University, Guangzhou 510006, People’s Republic of China, Fax: (+86)-20-39310187; Phone: (+86)-20-85210087School of Chemistry and Environment, South China Normal University, Guangzhou 510006, People’s Republic of China, Fax: (+86)-20-39310187; Phone: (+86)-20-85210087School of Chemistry and Environment, South China Normal University, Guangzhou 510006, People’s Republic of China, Fax: (+86)-20-39310187; Phone: (+86)-20-85210087School of Chemistry and Environment, South China Normal University, Guangzhou 510006, People’s Republic of China, Fax: (+86)-20-39310187; Phone: (+86)-20-85210087School of Chemistry and Environment, South China Normal University, Guangzhou 510006, People’s Republic of China, Fax: (+86)-20-39310187; Phone: (+86)-20-85210087School of Chemistry and Environment, South China Normal University, Guangzhou 510006, People’s Republic of China, Fax: (+86)-20-39310187; Phone: (+86)-20-85210087Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration of 3f was confirmed by X-ray crystallography.https://doi.org/10.3762/bjoc.5.53chiral bisphosphine ligandiridium catalystoxabicyclic alkenesring-opening reaction |
| spellingShingle | Dingqiao Yang Ping Hu Yuhua Long Yujuan Wu Heping Zeng Hui Wang Xiongjun Zuo Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles Beilstein Journal of Organic Chemistry chiral bisphosphine ligand iridium catalyst oxabicyclic alkenes ring-opening reaction |
| title | Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles |
| title_full | Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles |
| title_fullStr | Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles |
| title_full_unstemmed | Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles |
| title_short | Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles |
| title_sort | iridium catalyzed asymmetric ring opening reactions of oxabicyclic alkenes with secondary amine nucleophiles |
| topic | chiral bisphosphine ligand iridium catalyst oxabicyclic alkenes ring-opening reaction |
| url | https://doi.org/10.3762/bjoc.5.53 |
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