Chapter 1 14. (a) L. Hoang, S. Bahmanyar, K. N. Houk, B. List, J. Am. Chem. Soc. 2003, <strong>12</strong>5, 16-17; (b) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci U.S.A. 2004, 101, 5839-5842. 15. B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425. 16. F. Tanaka, R. Thayumanavan, C. F. Barbas III, J. Am. Chem. Soc. 2003, <strong>12</strong>5, 8523-8528. 17. B. List, J. Am. Chem. Soc. 2000, <strong>12</strong>2, 9336-9337. 18. B. List, J. Am. Chem. Soc. 2002, <strong>12</strong>4, 5656-5657. 19. N. Vignola, B. List, J. Am. Chem. Soc. 2004, <strong>12</strong>6, 450-451. 20. S. S.-Mossé, A. Alexakis, Chem. Commun. 2007, 30, 3<strong>12</strong>3-3135. 21. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. Int. Ed. 2005, 44, 42<strong>12</strong>-4215. 22. G.-L. Zhao, Y. Xu, H. Sundén, L. Eriksson, M. Sayah, A. Córdova, Chem. Commun. 2007, 734-735. 23. P. Melchiorre, K. A. Jørgensen, J. Org. Chem. 2003, 68, 4151-4157. 24. (a) M. T. Barros, A. M. F. <strong>Ph</strong>illips, Eur. J. Org. Chem. 2007, 178-185; (b) Y. Xu, A. Cόrdova, Chem. Commun. 2006, 460-462; (c) A. Lu, T. Liu, R. Wu, Y. Wang, G. Wu, Z. Zhou, J. Fang, C. Tang, J. Org. Chem. 2011, 76, 3872-3879. 25. (a) C.-L. Cao, M.-C. Ye, X.-L. Sun, Y. Tang, Org. Lett. 2006, 8, 2901-2904; (b) T. Mandal, C.-G. Zhao, Angew. Chem. Int. Ed. 2008, 47, 7714-7717; (c) F. Xue, L. Liu, S. Zhang, W. Duan, W. Wang, Chem. Eur. J. 2010, 16, 7979-7982; (d) H. Huang, E. N. <strong>Jacobs</strong>en, J. Am. Chem. Soc. 2006, <strong>12</strong>8, 7170-7171; (e) X. Jiang, Y. Zhang, A. S. C. Chan, R. Wang, Org. Lett. 2009, 11, 153-156; (f) D. A. Yalalov, S. B. Tsogoeva, S. Schmatz, Adv. Synth. Catal. 2006, 348, 826-832. 26. J. Wang, H. Li, B. Lou, L. Zu, H. Guo, W. Wang, Chem. Eur. J. 2006, <strong>12</strong>, 4321-4332. 27. B. Ni, Q. Zhang, K. Dhungana, A. D. Headley, Org. Lett. 2009, 11, 1037-1040. 28. N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas, J. Am. Chem. Soc. 2006, <strong>12</strong>8, 4966-4967. 29. T. Ishii, S. Fukioka, Y. Sekiguchi, H. Kotsuki, J. Am. Chem. Soc. 2004, <strong>12</strong>6, 9558-9559. 30. Vishnumaya, V. K. Singh, Org. Lett. 2007, 9, 1117-1119. 31. H. Pracejus, Justus Liebigs Ann. Chem. 1960, 634, 9-22. 32. S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599-602. 37
Chapter 1 33. B. Tan, X. Zeng, Y. Lu, P. J. Chua, G. Zhong, Org. Lett. 2009, 11, 1927-1930. 34. J. M. Betancort, C. F. Barbas, Org. Lett. 2001, 3, 3737-3740. 35. Z. Yang, J. Liu, X. Liu, Z. Wang, X. Feng, Z. Su, C. Hu, Adv. Synth. Catal. 2008, 350, 2001-2006. 36. D.-Q. Xu, L.-P. Wang, S.-P. Luo, Y.-F. Wang, S. Zhang, Z.-Y. Xu, Eur. J. Org. Chem. 2008, 6, 1049-1053. 37. S. Luo, H. Xu, X. Mi, J. Li, X. Zheng, J.-P. Cheng. J. Org. Chem. 2006, 71, 9244-9247. 38. T. Karthikeyan, S. Sankararaman, Tetrahedron: Asymmetry 2008, 19, 2741-2745. 39. T. Mandal, C.-G. Zhao, Tetrahedron Lett. 2007, 48, 5803-5806. 40. S. Chandrasekhar, B. Tiwari, B. B. Parida, C. R. Reddy, Tetrahedron: Asymmetry 2008, 19, 495-499. 41. G. Lv, R. Jin, W. Mai, L. Gao, Tetrahedron: Asymmetry 2008, 19, 2568-2572. 42. S. Luo, J. Li, L. Zhang, H. xu, J.-P. Cheng, Chem. Eur. J. 2008, 14, <strong>12</strong>73-<strong>12</strong>81. 43. Y. Xiong, Y. Wen, F. Wang, B. Gao, X. Liu, X. Huang, Adv. Synth. Catal. 2007, 349, 2156-2166. 44. (a) A. Lu, R. Wu, Y. Wang, Z. Zhou, G. Wu, J. Fang, C. Tang, Eur. J. Org. Chem. 2011, 1, <strong>12</strong>2-<strong>12</strong>7; (b) C. Yu, J. Qiu, F. Zheng, W. Zhong, Tetrahedron: Lett. 2011, 52, 3298- 3302; (c) A. Anwar, P.-H. Lee, T.-Y. Chou, C. Chang, K. Chen, Tetrahedron 2011, 76, 1171-1177. 45. (a) K.-J. Xiao, J.-M. Luo, K.-Y. Ye, Y. Wang, P.-Q. Huang, Angew. Chem. Int. Ed. 2010, 49, 3037-3040; (b) Y. Vo- Hoang, C. Gasse, M. Vidal, C. Garbay, H. Galon, Tetrahedron Lett. 2004, 45, 3603-3605. 46. (a) M. L. Curtin, R. B. Garland, H. R. Heyman, R. R. Frey, M. R. Michaelides, J. Li, L. J. Pease, K. B. Glaser, P. A. Marcotte, S. K. Davidsen, Bioorganic Med. Chem. Lett. 2002, <strong>12</strong>, 2919-2923; (b) B. J. Bradbury; M. Deshpande; A. Hashimoto; H. Y. Kim; E. Lucien; G. Pais; M. Pucci; Q. Wang; J. A. Wiles; A. <strong>Ph</strong>adke (Achillion <strong>Ph</strong>armaceuticals, Inc.), publication number: US 2010/02561<strong>12</strong> A1, 07 October 2010. 38
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Chapter 3 1 H NMR (400 MHz, CDCl 3
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Chapter 3 1 H NMR (400 MHz, CDCl 3
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Chapter 3 Please refer to α-ethyl
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Chapter 3 13 C NMR (100 MHz, CDCl 3
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Chapter 3 129.19, & 131.93 ppm repr
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Chapter 3 References 1. For the reg
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Chapter 3 19. The potassium complex
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Chapter 4 4.1 General information A
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Chapter 4 4.3 Racemate formation 4.
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Chapter 4 O NO 2 (S)-2-((R)-2-nitro
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Chapter 4 MS (EI), m/z (relative in
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Chapter 4 References 1. The two ena
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Chapter 5 5.1 General information R
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Chapter 5 5.2 Racemate formation To
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Chapter 5 The ee was determined by
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Chapter 5 (S)-1-(2,5-dioxo-1-phenyl
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Chapter 5 (S)-3-(benzo[d][1,3]dioxo
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Chapter 5 (S)-2,6-dimethyl-2-((S)-2
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Chapter 5 1 H NMR (400 MHz, CDCl 3
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Chapter 6 SPECTRA (HPLCs AND NMRs)
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Chapter 6 HPLC of 2,2,2-trifluoro-N
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Chapter 6 HPLC of 2-(2-nitro-1-p-to
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Chapter 6 HPLC of 2-(1-(furan-2-yl)
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Chapter 6 HPLC of 2,2-dimethyl-4-ni
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Chapter 6 HPLC of 3-(4-methoxypheny
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Chapter 6 HPLC of 2-(1-benzyl-2,5-d
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Chapter 6 HPLC of 1-(2,5-dioxo-1-ph
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Chapter 6 HPLC of 1-(2,5-dioxo-1-ph
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Chapter 6 HPLC of 2-(2,5-dioxo-1-ph
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Chapter 6 HPLC of 3-(benzo[d][1,3]d
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Chapter 6 HPLC of 2-methyl-2-(2,5-d
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Publication # 02 Sequential Reducti