本篇論文是探討三氟甲磺酸銅鹽[Cupric trifluoromethanesulfonate，Cu(OTf)2]催化還原醚化反應。在室溫下，分別以0.5 mol%銅三氟甲磺酸鹽為催化劑及三乙基矽烷為還原劑，三甲基矽醚可與羰基化合物在二氯甲烷中作用得到高產率的醚類衍生物。此外，我們也成功地將此條件應用在醣類分子的位向選擇性保護課題，可在葡萄醣化合物第三號氧原子位置順利引進苯甲基，對於朝向複雜多醣體的合成將會有所助益。

A Et3SiH-reductive etherification of the trimethylsilyl ethers with various carbonyl compounds in dichloromethane in excellent yields at room temperature employing 0.5 mol% Cu(OTf)2 as an efficient catalyst is described here. Regioselective O3-benzylation of the 4,6-O-benzylidene-2,3-di-O-trimethylsilyl- D-glucopyranosides to the corresponding 2-alcohols under this optimized set of conditions is also highlighted.

1. March, J. Advanced Organic Chemistry, Reactions, mechanisms and structure, 2nd ed.; McGraw-Hill Book Company, New York, 1978; pp 357-358 and references cited therein.
2. Hijfte, L. V.; Little, R. D. J. Org. Chem. 1985, 50, 3940-3942.
3. Doyle, M. P.; DeBruyn, D. J.; Kooistra, D. A. J. Am. Chem. Soc. 1972, 94, 3659-3661.
4. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1979, 48, 4679-4680.
5. Hatakeyama, S.; Mori, H.; Kitano, K.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1994, 35, 4367-4370.
6. Kato, J.-I.; Iwasawa, N.; Mukaiyama, T. Chem.Lett. 1985, 743-746.
7. Sassaman, M. B.; Kotian, K. D.; Surya Prakash, G. K.; Olah, G. A. J. Org. Chem. 1987, 52, 4314-4319.
8. Miura, K.; Ootsuka, K.; Suda, S.; Nishikori, H.; Hosomi, A. Synlett, 2002, 313-315.
9. Kawada, A.; Yasuda, K.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 2002, 50, 380-383.
10. Rai, A. N.; Basu, A. Tetrahedron Lett. 2003, 44, 2267-2269.
11. Lee, J.-C.; Tai, C.-A.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 851-855.
12. Wang, C.-C.; Luo, S.-Y.; Shie, C.-R.; Hung, S.-C. Org. Lett. 2002, 4, 847-849.
13. Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis 3rd Ed.; Wiley, New York, 1999.
14. Plante, O. J.; Buchward, S. L.; Seeberger, P. H. J Am. Chem. Soc. 2000, 122, 7148-7149.
15. (a) Classon, B.; Garegg, P. J.; Oscarson, S.; Tidén, A.-K. Carbohydr. Res. 1991, 216, 187-196. (b) Garegg, P. J.; KvarnStröm, I.; Niklasson, A.; Nikalasson, G.; Svensson, S. C. T. J. Carbohydr. Chem. 1993, 12, 933-953. (c) Jiang, L.; Chan, T.-H. J. Org. Chem. 1998, 63, 6035-6038.
16. Grindley, T. B. Adv. Carbohydr. Chem. Biochem. 1998, 53. 17-142.
17. Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Fan, H.-F.; Pai, C.-L.; Yang, W.-C.; Lu, L.-D.; Hung, S.-C. Angew. Chem. Int. Ed. 2002, 41, 2360-2362.