掌性三牙基胺基醇的製備及其在不對稱硼烷還原反應上的應用研究

Synthesis of Chiral Tridentate Aminoalcohols and Study of Their Application in Asymmetric Borane Reduction

葉書華(Shu-hua Yeh)

指導教授 ： 徐基東

朝陽科技大學/理工學院/應用化學系/碩士(2008年)

摘要

在不對稱硼烷還原反應中，oxazaborolidine化合物已被證實是個出色的掌性催化劑。許多掌性胺基醇及其衍生物都被當作起始物以用來製備合成oxazaborolidine。
我們實驗室以天然市售蒎烯(α-pinene)為起始物，合成一系列具N取代的胺基醇化合物。這些新型N取代胺基醇化合物被製備成oxaza-
borolidine後，作為反應中的催化劑，且應用在酮類的不對稱硼烷還原反應中。然而實驗的結果並非我們所預期的好，最後我們試著對此類反應的作用機制做些許的解釋以用來說明我們所得到的結果。

關鍵字

不對稱硼烷還原反應 ； 蒎烯 ； 掌性三牙基胺基醇

並列摘要

In asymmetric borane reduction of prochiral ketones to form chiral secondary alcohols, oxazaborolidine compounds have proved to be excellent chiral catalysts. Many chiral aminoalcohols and their derivatives have been used as starting materials for the synthesis of oxazaborolidines, either in isolated form or prepared in situ.
In our laboratory, we use natural α-pinene as a starting material to synthesize a series of novel N-substituted aminoalcohols. These newly prepared N-substituted aminoalcohols have been used to prepared oxazaborolidines as catalysts in the asymmetric borane reduction of prochiral ketones. The results are not as satisfactory as we anticipated; however, we have provided some possible explanation attempted to rationalize these results.

並列關鍵字

pinene ； asymmetric borane reduction ； chiral tridentate aminoalcohols

參考文獻

3. Asymmetric Synthesis ＆ Catalysis/楊登貴等編著, 1995, 1-2.

Chem. Soc. Perkin Trans. I 1985, 2039.

5. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109,

7. Masui, M.; Shioiri, T. SYNLETT 1996, 1, 49.

8. Markowicz, S. W.; Pokrzeptowicz, K. Tetrahedron: Asymmetry