基于吲哚啉的Cu催化不对称炔丙基烷基化及DDQ脱氢策略,成功合成了手性N-炔丙基吲哚化合物。通过使用一个结构刚性的酮亚胺三齿P,N,N-配体,反应获得了很好的对映选择性。该方法反应条件温和、底物适用范围广、产物收率高、立体选择性好,为手性N-炔丙基吲哚化合物的合成提供了一条简捷、高效的新途径。
The synthesis of optically active N‐propargylindoles has been accomplished via the Cu‐catalyzed asymmetric propargylic alkylation of indolines with propargylic esters, followed by the dehydro‐genation of the resulting N‐substituted indolines with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone. The reaction proceeded in good yield with high enantioselectivity under mild conditions using a bulky and structurally rigid tridentate ketimine P,N,N‐ligand, and exhibited a broad substrate scope.
参考文献
| [1] | Hattori G, Matsuzawa H, Miyake Y, Nishibayashi Y. Angew Chem Int Ed, 2008, 47:3781,2008. |
| [2] | Detz R J, Delville M M E, Hiemstra H, van Maarseveen J H. Angew Chem Int Ed, 2008, 47:3777,2008. |
| [3] | Nishibayashi Y. Synthesis, 2012, 44:489,2012. |
| [4] | Ding C H, Hou X L. Chem Rev, 2011, 111:1914,2011. |
| [5] | Fang P, Hou X L. Org Lett, 2009, 11:4612,2009. |
| [6] | Hattori G, Yoshida A, Miyake Y, Nishibayashi Y. J Org Chem, 2009, 74:7603,2009. |
| [7] | Hattori G, Miyake Y, Nishibayashi Y. ChemCatChem, 2010, 2:155,2010. |
| [8] | Hattori G, Sakata K, Matsuzawa H, Tanabe Y, Miyake Y, Nishi-bayashi Y. J Am Chem Soc, 2010, 132:10592,2010. |
| [9] | Detz R J, Abiri Z, le Griel R, Hiemstra H, van Maarseveen J H. Chem Eur J, 2011, 17:5921,2011. |
| [10] | Yoshida A, Ikeda M, Hattori G, Miyake Y, Nishibayashi Y. Org Lett, 2011, 13:592,2011. |
| [11] | Yoshida A, Hattori G, Miyake Y, Nishibayashi Y. Org Lett, 2011, 13:2460,2011. |
| [12] | Zhang C, Wang Y H, Hu X H, Zheng Z, Xu J, Hu X P. Adv Synth Catal,2012, 354:2854,2012. |
| [13] | Zhang C, Hu X H, Wang Y H, Zheng Z, Xu J, Hu X P. J Am Chem Soc, 2012, 134:9585,2012. |
| [14] | Mino T, Taguchi H, Hashimoto M, Sakamoto M. Tetrahedron:Asymmetry, 2013, 24:1520,2013. |
| [15] | Han F Z, Zhu F L, Wang Y H, Zou Y, Hu X H, Chen S, Hu X P. Org Lett, 2014, 16:588,2014. |
| [16] | Zhu F L, Zou Y, Zhang D Y, Wang Y H, Hu X H, Chen S, Xu J, Hu X P. Angew Chem Int Ed, 2014, 53:1410,2014. |
| [17] | Zou Y, Zhu F L, Duan Z C, Wang Y H, Zhang D Y, Cao Z, Zheng Z, Hu X P. Tetrahedron Lett, 2014, 55:2033,2014. |
| [18] | Shibata M, Nakajima K, Nishibayashi Y. Chem Commun, 2014, 50:7874,2014. |
| [19] | Zhu F L, Wang Y H, Zhang D Y, Hu X H, Chen S, Hou C J, Xu J, Hu X P. Adv Synth Catal, 2014, 356:3231,2014. |
| [20] | Zhu F L, Wang Y H, Zhang D Y, Xu J, Hu X P. Angew Chem Int Ed, 2014, 53:10223,2014. |
| [21] | Zhang D Y, Zhu F L, Wang Y H, Hu X H, Chen S, Hou C J, Hu X P. Chem Commun, 2014, 50:14459,2014. |
| [22] | Bandini M, Umani-Ronchi A. Catalytic Asymmetric Friedel-Crafts Alkylations. Weinheim:Wiley-VCH, 2009,2009. |
| [23] | Baran P S, Guerrero C A, Corey E J. J Am Chem Soc, 2003, 125:5628,2003. |
| [24] | Hayashi H, Takiuchi K, Murao S, Arai M. Agric Biol Chem, 1989, 53:461,1989. |
| [25] | Liu W B, Zhang X, Dai L X, You S L. Angew Chem Int Ed, 2012, 51:5183,2012. |
| [26] | Galm U, Hager M H, van Lanen S G, Ju J H, Thorson J S, Shen B. Chem Rev, 2005, 105:739,2005. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%