本論文主要探討以樟腦衍生之胺基醇與水楊醛衍生物縮合而得之三牙配位基與VO(acac)2所形成的掌性錯合物為催化劑，應用在不對稱亞□化反應上的研究。以1 mol%催化量的催化劑在0oC下，以H2O2為氧化劑，氧化硫醚化合物生成掌性亞□化合物，鏡像選擇性最好可達88% ee，且不會有□化合物的生成。而相較於其它的催化系統，本論文合成的催化劑使反應速度加快很多，惟產率略低。

This thesis dealt with the asymmetric oxidation of sulfide using in situ prepared chiral vanadium complex from tridentate ligands 100-112 with VO(acac)2.
The tridentate ligands were synthesized from camphor derived amino alcohols with salicyaldehyde derivates.
By using 1.0 eq hydrogen peroxide in portions with 1 mol% vanadium catalyst loading, the best result can be up to 88% ee. In most cases, although the enantioselectivity were moderate, yet the rate of sulfide oxidation was very fast compared with these reported in literature.

1.(a) Knowles, W. S.; Sabacky, M. J. J. Chem. Soc., Chem. Commun. 1968, 1445. (b) Noyori, R. Science 1990, 248, 1194. (c) Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
2.Kitamura, M.; Okada, G.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
3.Aggarwal, V. K.; Hynd, G.; Picoul, W.; Vasse, J. L. J. Am. Chem. Soc. 2002, 124, 9964.
4.黃全德博士論文，國立清華大學化學系，1999年。
5.Solladie, G. Synthesis 1981, 185.
6.Posner, G. H. Acc. Chem. Res. 1987, 20, 72.
7.Arai, Y.; Koizumi, T. Sulfur Rep. 1993, 15, 41.
8.Kosugi, H.; Konta, H.; Uda, H. J. Chem. Soc., Chem. Commun. 1985, 211.
9Lindberg, P.; Br□ndstorm, A.; Wallmark, B.; Mattson, H.; Rikner, L.; Hoffman, K. –J. Med. Res. Rev. 1990, 10, 1.
10.Matsugi, M.; Fukuda, N.; Minamikawa, J.-i.; Otsuka, S. Tetrahedron Lett. 1998, 35, 5591.
11.Miloskowski, C.; Solladie, G. Tetrahedron 1980, 36, 227.
12.(a) Marino, J. P.; Kim, M.-W.; Lawrence, R. J. Org. Chem. 1989, 54, 1784. (b) Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566. (c) Arai, Y.; Yamamoto, M.; Koizumi, T. Chem. Lett. 1986, 1225.
13.Arai, Y.; Yamamoto, M.; Koizumi, T. Bull. Chem. Soc., Jpn. 1988, 61, 467.
14.Andersen, K. K. Tetrahedron Lett. 1962, 93.
15.Colonna, S.; Gaggero, N.; Casella, L.; Carrea, G.; Pasta, P. Tetrahedron: Asymmetry 1992, 3, 95.
16.H. B. Kagan, in I. Ojima (Ed.), Catalytic Asymmetric Synthesis; VCH: Weinheim, 1993, pp. 203-226.
17.Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529.
18.Donnoli, M. I.; Superchi, S.; Rosini, C. J. Org. Chem. 1998, 63, 9392
19.Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1997, 62, 8560.
20.Palucki, M.; Handson, P.; Jacobsen, E. N. Tetrahedron Lett. 1992, 33, 7111.
21.Nagata, T.; Imagawa, K.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc., Jpn. 1995, 68, 3241.
22.Nakajima, K.; Kojima, M.; Toriumi, K.; Saito, K.; Fujita, J. Bull. Chem. Soc., Jpn. 1989, 62, 760.
23.Nakajima, K.; Kojima, K.; Kojima, M.; Fujita, J. Bull. Chem. Soc., Jpn. 1990, 63, 2620.
24.Bolm, C.; Bienewald, F. Angew. Chem. 1995, 107, 2883; Angew. Chem., In. Ed. Engl. 1995, 34, 2640.
25.Vetter, A. H.; Berkessel, A. Tetrahedron Lett. 1998, 39, 1741.
26.Pelotier, B.; Anson, M. S.; Campbell, I. B.; Macdonald, S. J. F.; Priem, G.; Jackson, R. F. W. Synlett 2002, 1055.
27.黃德仁博士論文，國立清華大學化學系，1999年。
28.陳培儂專題報告，國立清華大學化學系，2003年。
29.許筑婷碩士論文，國立清華大學化學系，2004年。
30.Robert, E.; Zhang, P. J. Org. Chem. 1996, 61, 8103.
31.Kouklovsky, C.; Pouilhes, A.; Langlois, Y. J. Am. Chem. Soc 1990, 112, 6672. (b) Malcolm R.; Blake, A. J.; Cadogan, J. I. G.; Doyle, A. A.; Gosney, I. Tetrahedron 1996, 52, 4079.
32.Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645.