我們利用樟腦(camphor)這個天然物以及它本身具有的不對稱中心當成起始物，並使用一系列非常具有立體選擇性的合成步驟，造就兩個新生成的不對稱中心，使它成為一個β-amino alcohol形式的chiral ligand，再將這個chiral ligand使用還原氨化反應加以衍生化，在過程中可能形成一個五環oxazolidine形式的產物，接著將其開環，使得在氮上能有不同的取代基，我們再拿這些chiral ligands進行Ru的催化不對稱氫化反應

Camphor is widely applied to catalytic asymmetric synthesis because of it’s two nature chiral center. We design and synthesis β-amino alcohol from camphor by a very highly stereoselecviv
-e route and then we modify several different substituent group on the nitrogen.
We achieve the goal by reductive amination because we want to get secondary amines. Instead of imines, we get the 5 member oxazolidine rings. Then open the rings, we obtain the desired
Compound.
Finally we apply the β-amino alcohols to the rutheniu catalytic asymmetric synthesis.

參考資料
1. Organic Chemistry;Bruice,P.Y.,3rd ed;Santa Barbara,2001.
2. Laurent,D.; Morris,S. Chem. Rev. 1993,93,763
3. Oguni,M.; Omi,T. Tetrahedron Lett. 1984,25,2823
4. Noyori, R.; Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T. J. Am. Chem. Soc. 1995, 117, 2675
5. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97
6. Alonsn, D. A.; Nordin, S. J. M.; Roth, P.; Tarnai, T.; Andersson, P. G. J. Org. Chem. 2000, 65, 3116
7. Hansen, K. B.; Chilenski, J. R.; Desmond, R.; Devine, P. N.; Grabowski, E. J. J.; Heid, R.; Kubryk, M.; Mathre, D. J.; Varsoloma, R. Tetrahedron Asymmetry 2003, 14, 3581
8. Sterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron Asymmetry 2002, 13, 2605
9. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521
10. Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Anderson, P. G . J. Am. Chem. Soc. 1999, 121, 9580
11. Bonner, M. P.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 1299
12. Tanaka, K.; Ushio, H.; Kawabata, Y.; Suzuki, H. J Chem. Soc. Perkin Trans 1 1991, 1445
13. Santhi, V.; Rao, J. M. Tetrahedron Asymmetry 2000, 11, 3553
14. Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron Asymmetry 2000, 11, 4127
15. Lerestif, J. M.; Perrocheau, J.; Tonnard, F.; Bazureau, J. P.; Hamelin, J. Tetrahedron 1995, 51, 6757
16. Saavedra, J. E. J. Org. Chem. 1985, 50, 2271
17. Roy, S.; Chakrabort, A. K. Tetrahedron Lett. 1998, 6355
18. Chittenden, R. A.; Cooper, G. H. J. Chem. Soc. C, 1970, 49
19. Davies, S. R.; Mitchell, M. C.; Cain, C. P.; Devitt, P, G.; Taylor, R. J.; Kee, T. P. J. Orgnomet. Chem. 1998, 550, 29
20. Denmark, S. E.; Rivera, I. J. Org. Chem. 1994, 59, 6887
21. Leautey, M.; Jubault, P.; Pannecoucke, X.; Quirion, J. C. Eur. J. Org. Chem. 2003, 3761