期刊文献+

氢化铝锂还原α,β-不饱和羰基化合物的新反应——一种合成1,3-二醇的简便方法 被引量:4

A Novel Practical Reaction of α,β-Unsaturated Esters and Ketones with Lithium Aluminum Hydride——A Facile Route to 1,3-Diols
在线阅读 下载PDF
导出
摘要 在 0℃下 ,以四氢呋喃为溶剂 ,用氢化铝锂还原α ,β 不饱和酯和酮 ,除得到正常的还原产物一醇外 ,还以适中的产率方便地得到 1,3 二醇 ,该反应原料易得 ,操作简单 ,有望应用于合成含有 1,3 A novel reaction of α,β-unsaturated esters and ketones with lithium aluminum hydride in dry tetrahydrofuran solution at 0 ℃ affords, in addition to saturated and unsaturated alcohols, the corresponding 1,3-diols in moderate yield. The utility of the transformation is available for staring materials. The synthetic routes are facile and the reactions can be performed on molar scales. Direct application can be expected in the synthesis of the natural products containing 1,3-diol structural unit.
出处 《化学学报》 SCIE CAS CSCD 北大核心 2003年第2期279-284,共6页 Acta Chimica Sinica
基金 国家自然科学基金 (创新研究群体基金 2 0 0 1 .1~ 2 0 0 3.1 2 )资助项目
关键词 Α Β-不饱和羰基化合物 氢化铝锂 还原反应 1 3-二醇 四氢呋喃 溶剂 lithium aluminum hydride, reduction, α,β-unsaturated esters and ketones, 1,3-diols
  • 相关文献

参考文献22

  • 1(a)Wasserman, H. H.; van Verth, J. E.; McCaustland, D.J.; Borowitz, I. J.; Kamber, B. J. Am. Chem. Soc. 1967,89, 1535.(b)Schlegel, R.; Thrum, H.; Zielinski, J.; Borowski, E. J.Antibiot. 1981, 34, 122.(c)Lipshutz, B. H.; Kozlowski, J. A. J. Org. Chem. 1984,49, 1147.(d)Kiyooka, S.-I.; Sasaoka, H.; Fujiyama, R. TetrahedronLett. 1984, 25, 5331.
  • 2(a)Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233.(b)Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A.J. Am. Chem. Soc. 1986, 108, 8279.(c)Kiyooka, S.-I.; Kuroda, H.; Shimasaki, Y. TetrahedronLett. 1986, 27, 3009.(d)Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic,O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155.(e)Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761.(f)Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M.Tetrahedron Lett. 1988, 29, 5419.(g)Ch^enevert, R.; Fortier, G.; Rhlid, R. B. Tetrahedron1992, 48, 6769.(h)Shimizu, M.; Yamada, S.; Fujita, Y.; Kobayashi, F.Tetrahedron : Asymmetry 2000, 11, 3883.(i)Angelaud, R.; Landais, Y. Tetrahedron 2000, 56, 2025.
  • 3(a)Hawker, C. J.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1992, 2459.(b)Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J.Am. Chem. Soc. 1991, 113, 4252.(c)Balagurusamy, V. S. K.; Ungar, G.; Percec, V.;Johansson, G. J. Am. Chem. Soc. 1997, 119, 1539.
  • 4Cao, X.-P.; Wang, F.; Guo, S. Synth. Commun. 2002, 32,3149.
  • 5Fuhrhop, J.; Penzlin, G. In Organic Synthesis, Ed.: Anton,U., VCH, New York, 1994, Chapter 2.1.
  • 6Jernigan, M. T.; Eliel, E. L. J. Am. Chem. Soc. 1995,177, 9638.
  • 7Robinson, C. N.; Horton, J. L.; Fosheé, D. O.; Jones, J.W.; Hanissian, S. H. J. Org. Chem. 1986, 51, 3535.
  • 8McElhanon, J. R.; Wu, M.-J.; Escobar, M.; Chaudhry, U.;Hu, C.-L.; McGrath, D. V. J. Org. Chem. 1997, 62, 908.
  • 9Li, L.-H.; Chan, T. H. Org. Lett. 2001, 3, 739.
  • 10Al-Farhan, E.; Keehn, P. M.; Stevenson, R. Synthesis 1992,959.

同被引文献49

引证文献4

二级引证文献4

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部