化学习题

Fukuyama-Yokoshima group meeting problem 16

本文作者:asymmboy

Chem-station小编继续为学习有机化学的各位同行带来Fukuyama-Yokoshima研究组反应机理问题的详细解答的第十六期。

问题 1

基本文献

[1] K. I. Booker-Milburn, J. K. Cowell, Tetrahedron Lett. 1996, 37, 2177. doi: 10.1016/0040-4039(96)00224-9.

相关链接: 四氧化钌

反应机理

参考文献

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[5] D. Johnston, K. N. Slessor, A. C. Oehlschlager, J. Org. Chem. 1985, 50, 114. doi: 10.1021/jo00201a022.

[6] B. Smith, III, B. A. Wexter, C. Y. Tu, J. P. Konepelski, J. Am. Chem. Soc. 1985, 107, 1308. doi: 10.1021/ja00291a034.

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[8] Kojima, Y. Inouye, H. Kakisawa, Bull. Chem. Soc. Jpn. 1985, 58, 1738. doi: 10.1246/bcsj.58.1738.

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[10]  D. Liu, C. W. Bielawski. Macromol. Rapid Commun. 2016, 37, 1587. doi: 10.1002/marc.201600336.

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[16] C. M. Rodríguez, J. M. Ode, J. M. Palazón, V. S. Martín, Tetrahedron1992, 48, 3571. doi: 10.1016/S0040-4020(01)88494-5.

[17] P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936. doi: 10.1021/jo00332a045.

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[23] M. Pedrón, L. Legnani, M.-A. Chiacchio, P. Caramella, T. Tejero, P. Merino. Beilstein J. Org. Chem. 2019, 15, 1552. doi: 10.3762/bjoc.15.158.

[24] J. M. Bakke, A. E. Frøhaug, J. Phys. Org. Chem.1996, 9, 310. doi: 10.1002/(SICI)1099-1395(199606)9:6<310::AID-POC790>3.0.CO;2-E.

[25] K. I. Booker-Milburn, J. K. Cowell, L. J. Harris, Tetrahedron. 1997, 53, 12319. doi: 10.1016/S0040-4020(97)00769-2.

[26] T. Bach, J. P. Hehn, Angew. Chem. Int. Ed. 2011, 50, 1000. doi: 10.1002/anie.201002845.

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问题 2

基本文献

[1] K. Wada, N. Kogure, M. Kitajima, Takayama, Tetrahedron Lett. 2019, 60, 187. doi: 10.1016/j.tetlet.2018.12.007.

反应机理

参考文献

[1] M. Azuma, T. Yoshikawa, N. Kogure, M. Kitajima, H. Takayama, J. Am. Chem.

Soc. 2014, 136, 11618. doi: 10.1021/ja507016g.

[2] H. Takayama, J. Syn. Org. Chem. Jpn. 2015, 73, 1072. doi: 10.5059/yukigoseikyokaishi.73.1072.

[3] A. Nakayama, N. Kogure, M. Kitajima, H. Takayama, Angew. Chem. Int. Ed. 2011, 50, 8025. doi: 10.1002/anie.201103550.

[4] A. Nakayama, M. Kitajima, H. Takayama, Synlett 2012, 23, 2014. doi: 10.1055/s-0032-1316680.

[5] H. Yang, R. G. Carter, L. N. Zakharov, J. Am. Chem. Soc. 2008, 130, 9238. doi: 10.1021/ja803613w.

[6] H. Yang, R. G. Carter, J. Org. Chem. 2010, 75, 4929. doi: 10.1021/jo100916x.

[7] D. A. Evans, J. R. Scheerer, Angew. Chem. Int. Ed. 2005, 44, 6038. doi: 10.1002/anie.200502296.

问题 3

基本文献

[1] S. Tsuchiya, H. Saito, K. Nogi, H. Yorimitsu, Org. Lett..2019, 21, 10, 3855. doi: 10.1021/acs.orglett.9b01353.

相关反应链接

Yorimitsu aromatic metamorphosis reaction

反应机理

参考文献

[1] D. Vasu, H. Yorimitsu, A. Osuka, Angew. Chem. Int. Ed. 2015, 54, 7162. doi: 10.1002/anie.201501992.

[2] S. HayateK. Nogi, H. Yormitsu, Chem. Lett. 2017, 46, 1122. doi: 10.1246/cl.170415.

[3] M. Bhanuchandra, K. Murakami, D. Vasu, H. Yorimitsu, A. Osuka, Angew.

Chem. Int. Ed. 2015, 54, 10234. doi: 10.1002/anie.201503671.

[4] M. Bhanuchandra, H. Yorimitsu, A. Osuka, Org. Lett. 2016, 18, 384. doi: 10.1021/acs.orglett.5b03384.

[5] M. Onoda, Y. Koyanagi, H. Saito, M. Bhanuchandra, Y. Matano, H. Yorimitsu,

Asian J. Org. Chem. 2017, 6, 257. doi: 10.1002/ajoc.201600612.

[6] S. Tsuchiya, H. Saito, K. Nogi, H. Yorimitsu, Org. Lett. 2017, 19, 5557. doi: 10.1021/acs.orglett.7b02660.

[7] H. Saito, S. Otsuka, K. Nogi, H. Yorimitsu, J. Am. Chem. Soc. 2016, 138,

  1. doi: 10.1021/jacs.6b10255.
[8] Y. Kurata, S. Otsuka, N. Fukui, K. Nogi, H. Yorimitsu, A. Osuka, Org. Lett. 2017, 19, 1274. doi: 10.1021/acs.orglett.6b03861.

[9] S. Tsuchiya, H. Saito, K. Nogi, H. Yorimitsu, Org. Lett. 2019, 21, 3855. doi: 10.1021/acs.orglett.9b01353.

[10] Y. Zhou, L. Lin,Y. Wang, J. Zhu, Q. Song, Org. Lett. 2019, 21, 7630. doi: 10.1021/acs.orglett.9b02933.

[11] H. Yorimitsu, D. Vasu, M. Bhanuchandra, K. Murakami, A. Osuka, Synlett

2016, 27, 1765. doi: 10.1055/s-0035-1561617.

[12] K. Nogi, H. Yorimitsu, Chem. Commun. 2017, 53, 4055. doi: 10.1039/C7CC00078B.

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