Enantioselective N-propargylation of indoles via Cu-catalyzed propargylic alkylation/dehydrogenation of indolines

Cuihua Xuebao/Chinese Journal of Catalysis

Volumn 36, Issue 1, 2015, Pages 86-92

  Zhu, Fulin ^a,b   Hu, Xiangping ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Asymmetric synthesis; Copper; Dehydrogenation; N propargylindole; Propargylic substitution

Indexed keywords

ALKYLATION; CATALYSIS; COPPER; DEHYDROGENATION;

2 ,3-DICHLORO-5 ,6-DICYANO-1 ,4-BENZOQUINONE; ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; N ,N-LIGAND; OPTICALLY ACTIVE; PROPARGYLATION; PROPARGYLIC ESTER;

ENANTIOSELECTIVITY;

EID: 84921919936     PISSN: 02539837     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1872-2067(14)60230-8     Document Type: Article

References (26)

1. Hattori G, Matsuzawa H, Miyake Y, Nishibayashi Y. Angew Chem Int Ed, 2008, 47: 3781
2. Detz R J, Delville M M E, Hiemstra H, van Maarseveen J H. Angew Chem Int Ed, 2008, 47: 3777
3. Nishibayashi Y. Synthesis, 2012, 44: 489
4. Ding C H, Hou X L. Chem Rev, 2011, 111: 1914
5. Fang P, Hou X L. Org Lett, 2009, 11: 4612
6. Hattori G, Yoshida A, Miyake Y, Nishibayashi Y. J Org Chem, 2009, 74: 7603
7. Hattori G, Miyake Y, Nishibayashi Y. ChemCatChem, 2010, 2: 155
8. Hattori G, Sakata K, Matsuzawa H, Tanabe Y, Miyake Y, Nishibayashi Y. J Am Chem Soc, 2010, 132: 10592
9. Detz R J, Abiri Z, le Griel R, Hiemstra H, van Maarseveen J H. Chem Eur J, 2011, 17: 5921
10. Yoshida A, Ikeda M, Hattori G, Miyake Y, Nishibayashi Y. Org Lett, 2011, 13: 592
11. Yoshida A, Hattori G, Miyake Y, Nishibayashi Y. Org Lett, 2011, 13: 2460
12. Zhang C, Wang Y H, Hu X H, Zheng Z, Xu J, Hu X P. Adv Synth Catal, 2012, 354: 2854
13. Zhang C, Hu X H, Wang Y H, Zheng Z, Xu J, Hu X P. J Am Chem Soc, 2012, 134: 9585
14. Mino T, Taguchi H, Hashimoto M, Sakamoto M. Tetrahedron: Asymmetry, 2013, 24: 1520
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
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
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
18. Shibata M, Nakajima K, Nishibayashi Y. Chem Commun, 2014, 50: 7874
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
20. Zhu F L, Wang Y H, Zhang D Y, Xu J, Hu X P. Angew Chem Int Ed, 2014, 53: 10223
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
22. Bandini M, Umani-Ronchi A. Catalytic Asymmetric Friedel-Crafts Alkylations. Weinheim: Wiley-VCH, 2009
23. Baran P S, Guerrero C A, Corey E J. J Am Chem Soc, 2003, 125: 5628
24. Hayashi H, Takiuchi K, Murao S, Arai M. Agric Biol Chem, 1989, 53: 461
25. Liu W B, Zhang X, Dai L X, You S L. Angew Chem Int Ed, 2012, 51: 5183
26. Galm U, Hager M H, van Lanen S G, Ju J H, Thorson J S, Shen B. Chem Rev, 2005, 105: 739