Catalytic asymmetric α-amination of α-branched ketones via enol catalysis

Synlett

Volumn 26, Issue 10, 2015, Pages 1413-1416

  Shevchenko, Grigory A ^a   Pupo, Gabriele ^a   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

asymmetric synthesis; azodicarboxylates; Bronsted acid catalysis; electrophilic amination; enol catalysis; branched ketones

Indexed keywords

ALKENE DERIVATIVE; ALPHA BRANCHED KETONE DERIVATIVE; AZODICARBOXYLIC ACID; CARBAMIC ACID; ENOL; KETONE DERIVATIVE; PHOSPHORIC ACID; REAGENT; UNCLASSIFIED DRUG;

ALPHA AMINATION; AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; ELECTROPHILICITY; ENANTIOSELECTIVITY; NITROGEN NITROGEN BOND; OXIDATION REDUCTION STATE;

EID: 84930377506     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0034-1380680     Document Type: Article

References (44)

1. Carrol F. I., Blough B. E., Abraham P., Mills A. C., Holleman J. A., Wolchenhauer S. A., Decker A. M., Landavazo A. K., McElroy T., Navarro H. A., Gatch M. B., Forster M. J. Med. Chem.: 2009; 52 6768
2. Tapping K. G. Eur. Patent EP0686629A3: 1999
3. Teall M. R. US Patent US5627211: 1997
4. Ager D. J., Prakash I., Schaad D. R. Chem. Rev.: 1996; 96 835
5. Klinger F. D. Acc. Chem. Res.: 2007; 40 1367
6. Reardon S. Nature (London): 2015; 517 130
7. Morgan C. J. A, Curran H. V. Addiction. 2011; 107 27
8. Blonk M. I., Koder B. G., van den Bemt P. M. L. A, Huygen F. J. P. M. Eur. J. Pain: 2010; 14 466
9. Adams H. A., Werner C. Der Anaesthesist: 1997; 46 1026
10. Hempelmann G., Kuhn D. F. M. Der Anaesthesist: 1997; 46 S3
11. Janey J. M. Angew. Chem. Int. Ed.: 2005; 44 4292
12. Vilaivan T., Bhanthumnavin W. Molecules: 2010; 15 917
13. Smith A. M. R, Hii K. K. Chem. Rev.: 2011; 111 1637
14. Zhou F., Liao F.-M, Yu J.-S, Zhou J. Synthesis: 2014; 46 2983
15. Saaby S., Bella M., Jorgensen K. A. J. Am. Chem. Soc.: 2004; 126 8120
16. Xu X., Yabuta T., Yuan P., Takemoto Y. Synlett: 2006; 137
17. Terada M., Nakano M., Ube H. J. Am. Chem. Soc.: 2006; 128 16044
18. He R., Wang X., Hashimoto T., Maruoka K. Angew. Chem. Int. Ed.: 2008; 47 9466
19. Terada M., Tsushima D., Nakano N. Adv. Synth. Catal.: 2009; 351 2817
20. Han X., Zhong F., Lu Y. Adv. Synth. Catal.: 2010; 352 2778
21. Xu C., Zhang L., Luo S. Angew. Chem. Int. Ed.: 2014; 53 4149
22. Xu C., Zhang L., Luo S. J. Org. Chem.: 2014; 79 11517
23. Nelson H. M., Patel J. S., Shunatona H. P., Toste F. D. Chem. Sci.: 2015; 6 170
24. List B. J. Am. Chem. Soc.: 2002; 124 5656
25. Bogevig A., Juhl K., Kumaragurubaran N., Zhuang W., Jorgensen K. A. Angew. Chem. Int. Ed.: 2002; 41 1790
26. Kumaragurubaran N., Juhl K., Zhuang W., Bogevig A., Jorgensen K. A. J. Am. Chem. Soc.: 2002; 124 6254
27. Vogt H., Vanderheiden S., Bräse S. Chem. Commun.: 2003; 2448
28. Hartmann C., Baumann T., Bächle M., Bräse S. Tetrahedron: Asymmetry: 2010; 21 1341
29. Fu J.-Y, Yang Q.-C, Wang Q.-L, Ming J.-N, Wang F.-Y, Xu H.-Y, Wang L.-X. J. Org. Chem.: 2011; 76 4661
30. Desmarchelier A., Yalgin H., Coeffard V., Moreau X., Greck X. Tetrahedron Lett.: 2011; 52 4430
31. Liu C., Zhu Q., Huang K.-W, Lu Y. Org. Lett.: 2011; 13 2638
32. Takeda T., Terada M. J. Am. Chem. Soc.: 2013; 135 15306
33. Felker I., Pupo G., Kraft P., List B. Angew. Chem. Int. Ed.: 2015; 54 1960
34. Zhang Z., Antilla J. C. Angew. Chem. Int. Ed.: 2012; 51 11778
35. Wang S.-G, Yin Q., Zhou C.-X, You S.-L. Angew. Chem. Int. Ed.: 2015; 54 647
36. Akiyama T., Katoh T., Mori K. Angew. Chem. Int. Ed.: 2009; 48 4226
37. Yamakana M., Hoshino M., Katoh T., Mori K., Akiyama T. Eur. J. Org. Chem.: 2012; 2012 4508
38. Guo Q.-X, Liu H., Guo C., Luo S.-W, Gu Y., Gong L.-Z. J. Am. Chem. Soc.: 2007; 129 3790
39. Pousse G., Le Cavalier F., Humphreys L., Rouden J., Blanchet J. Org. Lett.: 2010; 12 3582
40. During the preparation of this manuscript the Toste group independently published a very similar approach for the synthesis of enantioenriched α-branched α-amino ketones. See: Yang X., Toste F. D. J. Am. Chem. Soc.: 2015; 137 3205
41. Beattie C., North M. Molecules: 2011; 16 3420
42. Msutu A., Hunter R. Tetrahedron Lett.: 2014; 55 2295
43. Magnus P., Garizi N., Seibert K., Ornholt A. Org. Lett.: 2009; 11 5646
44. Magnus P., Brozell A. Org. Lett.: 2012; 14 3952