本篇論文敘述使用一價銠金屬及含有醯胺取代的掌性雙環[2.2.1]雙烯配基L2h所形成之催化劑，以1,4-二噁烷為溶劑，反應溫度為100 ℃，使用1 M碳酸氫鈉水溶液作為添加劑，針對含有α,β-不飽和烯酮之芳基硼酯化合物1進行不對稱分子內1,4-加成反應，生成一系列掌性3-芳基-1-二氫茚酮產物2。總共有27個例子，產率最高達到98%，鏡像超越值最高則是達到99%。
另外，利用3號位置具有芳基取代的掌性1-二氫茚酮化合物2g進行非鏡像選擇性酮基還原反應及胺化反應，可以順利合成(+)-Indatraline [(+)-7]藥物，兩步產率分別為77%及54%。

This thesis describes an enantioselective intramolecular 1,4-addition reactions of pinacolborate derivatives containing chalcones 1 in 1,4-dioxane at 100 ℃ employing aqueous sodium bicarbonate solution as an additive in presence of 3.0 mol% of Rh(I)-catalyst in situ generated from the [Rh(C2H4)2Cl]2 and the chiral bicyclo[2.2.1]heptadiene ligand bearing a diethyl amide group L2h. This synthetic protocol offers an easy way to obtain a series of chiral 3-aryl-1-indanone derivatives 2 in up to 98% yield and with up to 99% ee.

1. Zhong, C.; Zhu, J.; Chang, J.; Sun, X.; Tetrahedron Lett. 2011, 52, 2815−2817.
2. Clark, W. M.; TicknerEldridge, A. M.; Huang, G. K.; Pridgen, L. N.; Olsen, M. A.; Mills, R. J.; Lantos, I.; Baine, N. H. J. Am. Chem. Soc. 1998, 120, 4550−4551.
3. Bianco, G. G.; M. C. Ferraz, H. M. C.; Costa, A. M.; Costa-Lotufo, L. V.; Pessoa, C.; Moraes, M. O.; Schrems, M. G.; Pfaltz, A.; Silva, L. F. J. Org. Chem. 2009, 74, 2561–2566.
4. Froimowitz, M.; Wu, K.-M.; Moussa, A.; Haidar, R. M.; Jurayj, J.; George, C.; Gardner, E. L. J. Med. Chem. 2000, 43, 4981–4992.
5. Gabriele, B.; Mancuso, R.; Veltri, L. Chem. Eur. J. 2016, 22, 5056–5094.
6. Khoroshilova, O. V.; Vasilyev, A. V. Organics 2021, 2, 348–364.
7. Sharma, A. K.; Subramani, A. V.; Gorman, C. B. Tetrahedron, 2007, 63, 389–395.
8. Clark, W. M.; Kassick, A. J.; Plotkin, M. A.; Eldridge, A. M.; Lantos, I.; Baine, N. H. Org. Lett. 1999, 1, 1839–1842.
9. Smonou, I.; Orfanopoulos, M. Synth. Comm. 1990, 20, 1387–1397.
10. Wei, W.-T.; Yeh, J.-Y.; Kuo, T.-S.; Wu, H.-L. Chem. Eur. J. 2011, 17, 11405–11409.
11. Nørager, N. G.; Lorentz-Petersen, L. L. R.; Lyngso, L. O.; Kehler, J.; Juhl, K. Synlett. 2011, 12, 1753–1755.
12. Yu, Y.-N.; Xu, M.-H. J. Org. Chem. 2013, 78, 2736–2741.
13. Qin, X.; Lee, M. W. Y.; Zhou, J. S. Org. Lett. 2019, 21, 5990–5994.
14. Yue, G.; Lei, K.; Hajime, H.; Zhou, J. S. Angew. Chem. Int. Ed. 2015, 54, 6531–6535.
15. Minatti, A.; Zheng, X.; Buchwald, S. L. J. Org. Chem. 2007, 72, 9253−9258.
16. Yang, J.; Yoshikai, N. J. Am. Chem. Soc. 2014, 136, 16748–16751.
17. Kundu, K.; McCullagh, J. V.; Morehead, A. T., Jr. J. Am. Chem. Soc. 2005, 127, 16042–16043.
18. Rastelli, E. J.; Truong, N. T.; Coltart, D. M. Org. Lett. 2016, 18, 5588–5591.
19. Shintani, R.; Yashio, K.; Nakamura, T.; Okamoto, K.; Shimada, T.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 2772–2773.
20. Carreira, E. M.; Breitler, S. Synfacts. 2014, 10, 447.
21. Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579–5580.
22. Ueyama, K.; Tpkunaga, N.; Yoshida, K.; Hayashi, T. J. Am. Chem. Soc. 2003, 125, 11508–11509.
23. Syu, J.-F.; Lin, H.-Y.; Cheng, Y.-Y.; Tsai, Y.-C.; Ting, Y.-C.; Kuo, T.-S.; Janmanchi, D.; Wu, P.-Y.; Henschke, J. P.; Wu, H.-L. Chem. Eur. J. 2017, 23, 14515–14522.
24. Negus, S. S.; Brandt, M. R.; Mello, N. K. J. Pharmacol. Exp. Ther. 1999, 291, 60–69.
25. Davies, H. M.; Gregg, T. M. Tetrahedron Lett. 2002, 43, 4951–4953.
26. Roesner, S.; Casatejada, J. M.; Elford, T. G.; Sonawane, R. P.; Aggarwal, V. K. Org. Lett. 2011, 13, 5740–5743.
27. 邱奕文 (2021) 。碩士論文，國立臺灣師範大學化學系，臺北，臺灣。
28. Wu, Jianbing, et al. J. Med. Chem. 2021, 64, 10919–10933.
29. Xin, Y.; Zang, Z. H.; Chen, F. L. Synth. Commun. 2009, 39, 4062–4068.