Supporting Information
Experimental procedures and full characterization data for all the new compounds including optical rotations, IR, 1H NMR and 13C NMR, MS and elemental analysis are provided in the Supporting Information. In addition, X-ray structure data for compound 3f are given.
| Supporting Information File 1: Experimental and analytical data | ||
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Cite the Following Article
Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
Dingqiao Yang, Ping Hu, Yuhua Long, Yujuan Wu, Heping Zeng, Hui Wang and Xiongjun Zuo
Beilstein J. Org. Chem. 2009, 5, No. 53.
https://doi.org/10.3762/bjoc.5.53
How to Cite
Yang, D.; Hu, P.; Long, Y.; Wu, Y.; Zeng, H.; Wang, H.; Zuo, X. Beilstein J. Org. Chem. 2009, 5, No. 53. doi:10.3762/bjoc.5.53
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- Kumar, S. V.; Yen, A.; Lautens, M.; Guiry, P. J. Catalytic asymmetric transformations of oxa- and azabicyclic alkenes. Chemical Society reviews 2021, 50, 3013–3093. doi:10.1039/d0cs00702a
- Pounder, A.; Ho, A.; Macleod, M.; Tam, W. Chemistry of Unsymmetrical C1-Substituted Oxabenzonorbornadienes. Current organic synthesis 2021, 18, 446–474. doi:10.2174/1570179417666210105121115
- Sifeng, L.; Zihao, W.; Xiao, H.; Bian, Z.; Wang, J. J. Enantioselective synthesis of indole derivatives by Rh/Pd relay catalysis and their anti-inflammatory evaluation. Chemical communications (Cambridge, England) 2020, 56, 7573–7576. doi:10.1039/d0cc03158e
- Chen, T.; Gan, L.; Wang, R.; Deng, Y.; Peng, F.; Lautens, M.; Shao, Z. Rhodium(I)/Zn(OTf)2‐Catalyzed Asymmetric Ring Opening/Cyclopropanation of Oxabenzonorbornadienes with Phosphorus Ylides. Angewandte Chemie 2019, 131, 15966–15970. doi:10.1002/ange.201909596
- Chen, T.; Gan, L.; Wang, R.; Deng, Y.-H.; Peng, F.; Lautens, M.; Shao, Z. Rhodium(I)/Zn(OTf)2 -Catalyzed Asymmetric Ring Opening/Cyclopropanation of Oxabenzonorbornadienes with Phosphorus Ylides. Angewandte Chemie (International ed. in English) 2019, 58, 15819–15823. doi:10.1002/anie.201909596
- Hill, J.; Wicks, C.; Pounder, A.; Tam, W. Iridium-catalyzed ring-opening reactions of unsymmetrical oxabenzonorbornadienes with water and alcohol nucleophiles. Tetrahedron Letters 2019, 60, 150990. doi:10.1016/j.tetlet.2019.150990
- Boutin, R.; Koh, S.; Tam, W. Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene. Current organic synthesis 2019, 16, 460–484. doi:10.2174/1570179416666181122094643
- Luo, R. s.; Cheng, G.; Wei, Y.-F.; Deng, R.; Huang, M.; Liao, J. Enantioselective Iridium-Catalyzed Ring Opening of Low-Activity Azabenzonorbornadienes with Amines. Organometallics 2018, 37, 1652–1655. doi:10.1021/acs.organomet.8b00239
- Cheng, G.; Yang, W.; Li, Y.; Yang, D. Iridium/Copper Co-catalyzed Anti-Stereoselective Ring Opening of Oxabenzonorbornadienes with Grignard Reagents. The Journal of organic chemistry 2016, 81, 7817–7823. doi:10.1021/acs.joc.6b01479
- Šunjić, V.; Peroković, V. P. Retrosynthetic Considerations and Syntheses of Complex, Biologically Active Molecules. Organic Chemistry from Retrosynthesis to Asymmetric Synthesis; Springer International Publishing, 2016; pp 189–211. doi:10.1007/978-3-319-29926-6_9
- Zhou, Y.; Lu, Z.; Han, B.; Zeng, C.; Zhang, Z.; Fan, B. Iridium-catalyzed highly enantioselective ring opening reaction of oxabenzonorbornadienes with amines. Tetrahedron: Asymmetry 2015, 26, 1354–1359. doi:10.1016/j.tetasy.2015.10.017
- Yang, W.; Luo, R.; Yang, D. Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles. Molecules (Basel, Switzerland) 2015, 20, 21103–21124. doi:10.3390/molecules201219748
- Li, S.; Xu, J.; Fan, B.; Lu, Z.; Zeng, C.; Bian, Z.; Zhou, Y.; Wang, J. Palladium/Zinc Co-Catalyzed syn-Stereoselectively Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Phenols. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 21, 9003–9007. doi:10.1002/chem.201500816
- Meng, L.; Yang, W.; Pan, X.; Tao, M.; Cheng, G.; Wang, S.; Zeng, H.; Long, Y.; Yang, D. Platinum-catalyzed asymmetric ring-opening reactions of oxabenzonorbornadienes with phenols. The Journal of organic chemistry 2015, 80, 2503–2512. doi:10.1021/acs.joc.5b00065
- Yu, L.; Zhou, Y.; Xu, X.; Li, S.; Xu, J.; Fan, B.; Lin, C.; Bian, Z.; Chan, A. S. C. Asymmetric ring opening reaction of oxabenzonorbornadienes with amines promoted by iridium / NMDPP complex. Tetrahedron Letters 2014, 55, 6315–6318. doi:10.1016/j.tetlet.2014.09.089
- Zeng, Z.; Yang, D.; Long, Y.; Pan, X.; Huang, G.; Zuo, X.; Zhou, W. Nickel-catalyzed asymmetric ring opening of oxabenzonorbornadienes with arylboronic acids. The Journal of organic chemistry 2014, 79, 5249–5257. doi:10.1021/jo500821m
