臺灣博碩士論文加值系統

本篇論文探討藉由本實驗室發展之對胺基醇進行手性分離方式，用以建構手性2,6-二取代哌啶。另外，以引入手性輔助基的方式合成手性 7-氮雜降冰片烷之衍生物。

Studies on syntheses of enantiomeric pure 2,6-piperidine derivatives by chiral resolution of aminoalcohol. Syntheses of enantiomeric pure 7-azanorborane derivatives by using chiral auxiliary.

第一章 關於手性2,6-二取代哌啶衍生物之合成研究 1
1.1 2, 6-二取代哌啶衍生物的介紹 1
1.2 手性2, 6-二取代哌啶衍生物之合成研究 5
第二章 關於手性 7-氮雜降冰片烷衍生物之合成研究 11
2.1 7-氮雜降冰片烷衍生物的介紹 11
2.2 手性7-氮雜降冰片烷衍生物之合成研究 15
第三章 銠催化之成環性甲醯化反應之研究 21
3.1 骨牌式反應 21
3.2 利用氫甲醯化反應進行骨牌式反應 23
3.2.1 歷史回顧 23
3.2.2 結果與討論 26
第四章 實驗部分 31
4.1 儀器測定與試劑 31
4.2 實驗步驟 33
第五章 參考文獻 65
第六章 圖譜資料 69

1. F.-X. Felpin and J. Lebreton, Eur. J. Org. Chem., 2003, 3693–3712.
2. C. Tanret, Compt. Rend. 1878, 86, 1270.
3. R. E. Gilman and L. Marion, Bull. Soc. Chim. Fr. 1961, 1993–1995.
4. R. W. Bates and K. Sa-Ei, Tetrahedron, 2002, 58, 5957–5978.
5. O. Meth-Cohn; C.-Y. Yu; P. Lestage; M.-C. Lebrun; D.-H. Cagniard and P. Renard, Eur. Pat. 1050531, 2000.
6. C. J. Smith; A. B. Holmes and N. J. Press, Chem. Comm., 2002, 1214–1215.
7. (a) P. D. Bailey; P. A. Millwood and P. D. Smith, Chem. Comm., 1998, 633–640. (b) J. N. Tawara; A. Blokhin; T. A. Foderaro and F. R. Stermitz, J. Org. Chem., 1993, 58, 4813–4818.
8. S. G. Davies; K. Iwamoto; C. A. P. Smethurst; A. D. Smith; H. Rodriguez-Solla, Synlett 2002, 1146–1148.
9. S. G. Pyne; P. Bloem; S. L. Chapman; C. E. Dixon and R. Griffith, J. Org. Chem. 1990, 55, 1086–1093.
10. S. Najdi and M. J. Kurth, Tetrahedron Lett. 1990, 31, 3279–3282.
11. T. F. Spande; H. M. Garraffo; M. W. Edwards; H. J. C. Yeh; L. Pannel and J. W. Daly, J. Am. Chem. Soc. 1992, 114, 3475–3478.
12. J. P. Sullivan; M. W. Decker; J. D. Brioni; D. Donnelly-Roberts; D. J. Anderson; A. W. Bannon; C.-H. Kang; P. Adams; M. Piattoni-Kaplan; J. J. Buckley; M. Gopalakrishnan; M. Williams and S. P. Arneric, J. Pharmacol Exp. Ther. 1994, 8, 624–631.
13. F. Carroll; J. Lee; A. N. H. Hernan; M. Wei; L. Brieaddy; P. Abraham; M. Damaj and B. Martin, J. Med. Chem. 2002, 45, 4755–4761.
14. E. J. Corey; T.-P. Loh; S. AchyuthaRao; D. C. Daley and S. Sarshar, J. Org. Chem. 1993, 58, 5600–5602.
15. C. Zhang and M. L. Trudell, J. Org. Chem. 1996, 61, 7189–7191.
16. D. Bai; R. Xu; G. Chu and X. Zhu, J. Org. Chem. 1996, 61, 4600–4606.
17. 作法參考：高煜凱, Studies on Asymmetric Reactions Catalyzed by Chiral 1,2-aminoalcohol. 碩士論文. 台中：國立中興大學理學院化學研究所.
18. (a) R. Robinson, J. Chem. Soc. 1917, 111, 762–768. (b) C. Schöpf and G. Lehmann, Ann. Chem., 1935, 1, 518.
19. O. Affolter; A. Baro; W. Frey and S. Laschat, Tetrahedron 2009, 65, 6626–6634.
20. L. F. Tietze, Chem. Rev. 1996, 1, 115–116.
21. O. Abillard and B. Breit, Adv. Synth. Catal. 2007, 349, 1891–1895.
22. R.-G. Han; Y. Wang; Y.-Y. Li and P.-F. Xu, Adv. Synth. Catal. 2008, 350, 1474–1478.
23. W.-H. Chiou; G.-H. Lin; C.-C Hsu; S. T. Chaterpaul and I. Ojima, Org. Lett. 2009, 11, 2659–2662.
24. 林益暉, A Novel Alkyne-mediated Rh-Catalyzed Cyclohydrocarbonylation: Application to Synthesis of (±)-Tashiromine. 碩士論文. 台中：國立中興大學理學院化學研究所.
25. 由酯類水解成酸與支鏈胺進行耦合反應而得，作法同 26a；支鏈胺的製備參考：(a) C. E. Anderson; L. E. Overman and M. P. Watson, Org. Syn. 2005, 82, 134–139. (b) L. E. Overman, J. Am. Chem. Soc. 1976, 98, 2901–2910. (c) H. Nomura and C. J. Richards, Org. Lett. 2009, 11, 2892–2895.
26. J. E. Burks, Jr.; L. Espinosa; E. S. LaBell; J. M. McGill; A. R. Ritter; J. L. Speakman and M. A. Williams, Organic Process Research & Development 1997, 1, 198–210.
27. C. R. Davis; R. A. Johnson; J. I. Cialdella; W. F. Liggett; S. A. Mizsak and V. P. Marshall, J. Org. Chem. 1997, 62, 2244–2251.
28. A. T. Evelyn and F. T. Leewo, Eur. Pat. 074292, 2004.
29. J. R. Falck; A. He; H. Fukui; H. Tsutsui and A. Radha, Angew. Chem. Int. Ed. 2007, 46, 4527–4529.