Bi(OTf)3-Catalyzed One-Step Catalytic Synthesis of N-Boc or N-Cbz Protected α-Branched Amines

Journal of Organic Chemistry

Volumn 80, Issue 1, 2015, Pages 559-567

  Jaratjaroonphong, Jaray ^a   Tuengpanya, Surisa ^a   Ruengsangtongkul, Sureeporn ^a  

^a BURAPHA UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES;

BISMUTH TRIFLATE; CATALYTIC LOADING; CATALYTIC SYNTHESIS; MILD REACTION CONDITIONS; ONE POT; ONE STEP SYNTHESIS; PROTECTIVE GROUP; THREE-COMPONENT COUPLING REACTION;

BISMUTH COMPOUNDS;

ALDEHYDE; AMINE; AROMATIC COMPOUND; BENZYL CARBAMATE; BENZYL[(2,4,6 TRIMETHOXYPHENYL) 2 METHYLLPROPYL]CARBAMATE; BENZYL[(2,4,6 TRIMETHOXYPHENYL)PHENYLMETHYL]CARBAMATE; BISMUTH DERIVATIVE; BISMUTH TRIFLATE; CARBAMIC ACID DERIVATIVE; TERT BUTYLPHENYL(2,4,6 TRIMETHOXYPHENYL)METHYLCARBAMATE; TERT BUTYL[(2,4,5 TRIMETHOXYPHENYL)PHENYLMETHYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL) 2 FLUOROPHENYLMETHYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL) 2 METHYLPROPYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL) 3 METHYLBUTYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL) 3 PHENYLPROPYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL) 4 BROMOPHENYLMETHYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL) 4 CHLOROPHENYLMETHYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL) 4 FLUOROPHENYLMETHYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL) 4 METHOXYPHENYLMETHYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL) 4 NITROPHENYLMETHYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL)CYCLOHEXYLMETHYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL)CYCLOPENTYLMETHYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL)CYCLOPROPYLMETHYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL)PENTYL]CARBAMATE; TERT BUTYL[(2,4,6 TRIMETHOXYPHENYL)PROPYL]CARBAMATE; TERT BUTYL[2 (5 ETHYLFURYL)PHENYLMETHYL]CARBAMATE; TERT BUTYL[2 (5 ETHYLTHIENYL)PHENYLMETHYL]CARBAMATE; TERT BUTYL[2 (5 METHYLFURYL)PHENYLMETHYL]CARBAMATE; TERT BUTYL[2 (5 METHYLTHIENYL)PHENYLMETHYL]CARBAMATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; BI(OTF)3; MESYLIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; REACTION OPTIMIZATION; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMINES; CATALYSIS; MESYLATES; MOLECULAR STRUCTURE;

EID: 84924239703     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502540k     Document Type: Article

References (69)

1. Rosen, T. J.; Coffman, K. J.; McLean, S.; Crawford, R. T.; Bryce, D. K.; Gohda, Y.; Tsuchiya, M.; Nagahisa, A.; Nakane, M.; Lowe, J. A., III Bioorg. Med. Chem. Lett. 1998, 8, 281-284
2. Kogen, H.; Toda, N.; Tago, K.; Marumoto, S.; Takami, K.; Ori, M.; Yamada, N.; Koyama, K.; Naruto, S.; Abe, K.; Yamazaki, R.; Hara, T.; Aoyagi, A.; Abe, Y.; Kaneko, T. Org. Lett. 2002, 4, 3359-3362
3. Selvam, N. P.; Perumal, P. T. Tetrahedron Lett. 2006, 47, 7481-7483
4. Gall, E. L.; Haurena, C.; Sengmany, S.; Martens, T.; Troupel, M. J. Org. Chem. 2009, 74, 7970-7973
5. Meyet, C. E.; Pierce, C. J.; Larsen, C. H. Org. Lett. 2012, 14, 964-967
6. Smith, M. B. Organic Synthesis; McGraw-Hill: New York, 1994; p 1331.
7. Heaney, H. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 733.
8. Roberts, R. M.; Khalaf, A. A. Friedel-Crafts Alkylation Chemistry. A Century of Discovery; Dekker: New York, 1984.
9. Olah, G. A. Friedel-Crafts Chemistry; Wiley-Interscience: New York, 1973.
10. Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804-11805
11. Jia, Y.-X.; Xie, J.-H.; Duan, H.-F.; Wang, L.-X.; Zhou, Q.-L. Org. Lett. 2006, 8, 1621-1624
12. Kang, Q.; Zhao, Z.-A.; You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484-1485
13. Sun, F.-L.; Zheng, X.-J.; Gu, Q.; He, Q.-L.; You, S.-L. Eur. J. Org. Chem. 2010, 47-50
14. Weix, D. J.; Shi, Y.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 1092-1093
15. Nakagawa, H.; Rech, J. C.; Sindelar, R. W.; Ellman, J. Org. Lett. 2007, 9, 5155-5157
16. Yang, H.; Cui, B.; Wu, G.; Miao, Z.; Chen, R. Tetrahedron 2012, 68, 4830-4837
17. Li, G.-X.; Qu, J. Chem. Commun. 2012, 48, 5518-5520
18. Feng, J.; Yan, W.; Wang, D.; Li, P.; Sun, Q.; Wang, R. Chem. Commun. 2012, 48, 8003-8005
19. Janczuk, A.; Zhang, W.; Xie, W.; Lou, S.; Cheng, J.; Wang, P. G. Tetrahedron Lett. 2002, 43, 4271-4274
20. Jiang, B.; Huang, Z.-G. Synthesis 2005, 2198-2204
21. Soueidan, M.; Collin, J.; Gil, R. Tetrahedron Lett. 2002, 47, 5467-5470
22. Gong, Y.; Kato, K.; Kimoto, H. Synlett 2000, 1058-1060
23. Gong, Y.; Kato, K. Tetrahedron: Asymmetry 2001, 12, 2121-2127
24. Temelli, B.; Unaleroglu, C. Tetrahedron Lett. 2005, 46, 7941-7943
25. Temelli, B.; Unaleroglu, C. Tetrahedron 2006, 62, 10130-10135
26. Esquivias, J.; Gómez-Arrayás, R.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 629-633
27. Alonso, I.; Esquivias, J.; Gómez-Arrayás, R.; Carretero, J. C. J. Org. Chem. 2008, 73, 6401-6404
28. Liu, C.-R.; Li, M. B.; Yang, C. F.; Tian, S.-K. Chem. Commun. 2008, 1249-1251
29. Thirupathi, P.; Kim, S. S. J. Org. Chem. 2010, 75, 5240-5249
30. Chatterjee, P. N.; Maity, A. K.; Mohapatra, S. S.; Roy, S. Tetrahedron 2013, 69, 2816
31. Thirupathi, P.; Kim, S. S. Eur. J. Org. Chem. 2010, 1798-1808
32. Das, B.; Laxminarayana, K.; Ravikanth, B.; Rao, B. R. J. Mol. Catal. A: Chem. 2007, 261, 180-183
33. Patil, S. B.; Singh, P. R.; Surpur, M. P.; Samant, S. D. Ultrason. Sonochem. 2007, 14, 515-518
34. Zhang, P.; Zhang, Z.-H. Monatsh. Chem. 2009, 140, 199-203
35. Hajipour, A. R.; Ghayeb, Y.; Sheikhan, N.; Ruoho, A. E. Tetrahedron Lett. 2009, 50, 5649-5651
36. Lei, M.; Ma, L.; Hu, L. Tetrahedron Lett. 2009, 50, 6393-6397
37. Kumar, A.; Kumar, M.; Gupta, M. K. Tetrahedron Lett. 2009, 50, 7024-7027
38. Nandi, G. C.; Samai, S.; Kumar, R.; Singh, M. S. Tetrahedron Lett. 2009, 50, 7220-7222
39. Wang, M.; Liang, Y.; Zhang, T. T.; Gao, J. J. Chin. Chem. Lett. 2012, 23, 65
40. Safari, J.; Zarnegar, Z. J. Ind. Eng. Chem. 2014, 20, 2292-2297
41. Shaterian, H. R.; Hosseinian, A.; Ghashang, M. Tetrahedron Lett. 2008, 49, 5804-5806
42. Shaterian, H. R.; Hosseinian, A.; Ghashang, M. Synth. Commun. 2009, 39, 2560-2574
43. Shaterian, H. R.; Hosseinian, A.; Ghashang, M. Chin. J. Chem. 2009, 27, 821-824
44. Tavakoli-Hoseini, N.; Heravi, M. M.; Bamoharram, F. F.; Davoodnia, A. Bull. Korean Chem. Soc. 2011, 32, 787-792
45. Bensel, N.; Pevere, V.; Desmurs, J. R.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 879
46. Joshi, N. S.; Whitaker, L. R.; Francis, M. B. J. Am. Chem. Soc. 2004, 126, 15942
47. Halli, J.; Manolikakes, G. Eur. J. Org. Chem. 2013, 7471-7475
48. Shirakawa, S.; Kobayashi, S. Org. Lett. 2006, 8, 4939-4942
49. Jaratjaroonphong, J.; Krajangsri, S.; Reutrakul, V. Tetrahedron Lett. 2012, 53, 2476-2479
50. Bothwell, J. M.; Krabbe, S. W.; Mohan, R. S. Chem. Soc. Rev. 2011, 40, 4649-4707
51. Leonard, N. M.; Wieland, L. C.; Mohan, R. S. Tetrahedron 2002, 58, 8373-8397
52. Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227-2302
53. Ollevier, T.; Nadeau, E. J. Org. Chem. 2004, 69, 9292-9295
54. Schneider, A. E.; Manolikakes, G. Synlett 2013, 24, 2057-2060
55. Schneider, A. E.; Beisel, T.; Shemet, A.; Manolikakes, G. Org. Biomol. Chem. 2014, 12, 2356-2359
56. Jaratjaroonphong, J.; Sathalalai, S.; Techasauvapak, P.; Reutrakul, V. Tetrahedron Lett. 2009, 50, 6012-6015
57. Jaratjaroonphong, J.; Tuengpanya, S.; Saeeng, R.; Udompong, S.; Srisook, K. Eur. J. Med. Chem. 2014, 83, 561-568
58. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77
59. Rad-Moghadam, K.; Sharifi-Kiasaraie, M. Tetrahedron 2009, 65, 8816-8820
60. Ji, S.-J.; Wang, S.-Y.; Zhang, Y.; Loh, T.-P. Tetrahedron 2004, 60, 2051-2055
61. Green, W.; Wats, M. P. G. Protecting Groups in Organic Synthesis, 2nd ed.; John Wiley and Sons: New York, 1999.
62. Gibson, F. S.; Bergmeier, S. C.; Rapoport, H. J. Org. Chem. 1994, 59, 3216-3218
63. Daga, M. C.; Teddei, M.; Varchi, G. Tetrahedron Lett. 2001, 42, 5191-5194
64. Li, B.; Bemish, R.; Buzon, R. A.; Chiu, C. K.-F.; Colgan, S. T.; Kissel, W.; Le, T.; Leeman, K. R.; Newell, L.; Roth, J. Tetrahedron Lett. 2003, 44, 8113-8115
65. Wang, G.; Li, C.; Li, J.; Jia, X. Tetrahedron Lett. 2009, 50, 1438-1440
66. Nair, V.; Abhilash, K. G.; Vidya, N. Org. Lett. 2005, 7, 5857-5859
67. Chandrasekhar, S.; Khatun, S.; Rajesh, G.; Reddy, C. R. Tetrahedron Lett. 2009, 50, 6693-6697
68. Thirupathi, P.; Kim, S. S. J. Org. Chem. 2010, 75, 5240-5249
69. Nair, V.; Vidya, N.; Abhilash, K. G. Synthesis 2006, 3647-3652