A novel method for synthesizing 3-arylpyrrolidine and 4-arylpiperidine derivatives through an acid-promoted skeletal rearrangement

Tetrahedron Letters

Volumn 54, Issue 12, 2013, Pages 1562-1565

  Yokosaka, Takuya ^a   Nemoto, Tetsuhiro ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Aza Prins reaction; ipso Friedel Crafts reaction; Piperidine; Pyrrolidine; Skeletal rearrangement

Indexed keywords

3 ARYLPYRROLIDINE DERIVATIVE; 4 ARYLPIPERIDINE DERIVATIVE; CARBON; CATION; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; COVALENT BOND; DRUG STRUCTURE; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SKELETAL REARRANGEMENT; STEREOCHEMISTRY;

EID: 84873702576     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.01.034     Document Type: Article

References (53)

1. Reviews on chemistry and biology of pyrrolidines and piperidines, see F.J. Sardina, and H. Rapoport Chem. Rev. 96 1996 1825 1872
2. D. O'Hagan Nat. Prod. Rep. 17 2000 435 446
3. J.W. Daly, T.F. Spande, and H.M. Garraffo J. Nat. Prod. 68 2005 1556 1575
4. F. Bellina, and R. Rossi Tetrahedron 62 2006 7213 7256
5. For recent selected examples of the synthesis of pyrrolidines and piperidines, see R.L. LaLonde, B.D. Sherry, E.J. Kang, and F.D. Toste J. Am. Chem. Soc. 129 2007 2452 2453
6. E.C. Carlson, L.K. Rathbone, H. Yang, N.D. Collett, and R.G. Carter J. Org. Chem. 73 2008 5155 5158
7. H.-C. Xu, and K.D. Moeller J. Am. Chem. Soc. 132 2010 2839 2844
8. Z. Cui, H.-J. Yu, R.-F. Yang, W.-Y. Gao, C.-G. Feng, and G.-Q. Lin J. Am. Chem. Soc. 133 2011 12395 12397
9. P. Mukherjee, and R.A. Widenhoefer Org. Lett. 13 2011 1334 1337
10. T.W. Liwosz, and S.R. Chemler J. Am. Chem. Soc. 134 2012 2020 2023
11. T. Seki, S. Tanaka, and M. Kitamura Org. Lett. 14 2012 608 611
12. B. Olszewska, B. Kryczka, and A. Zawisza Tetrahedron Lett. 53 2012 6826 6829
13. For a review, see N.G. Gunasekara, S. Noble, and P. Benfield Drugs 55 1998 85 120
14. For a review on the synthesis of paroxetine, see C. De Risi, G. Fanton, G.P. Pollini, C. Trapella, and V. Zanirato Tetrahedron: Asymmetry 19 2008 131 155
15. For examples of catalytic asymmetric synthesis of paroxetine, see T. Senda, M. Ogasawara, and T. Hayashi J. Org. Chem. 66 2001 6852 6856
16. M.S. Taylor, and E.N. Jacobsen J. Am. Chem. Soc. 125 2003 11204 11205
17. G. Hughes, M. Kimura, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 11253 11258
18. S. Brandau, A. Landa, J. Franzén, M. Marigo, and K.A. Jørgensen Angew. Chem., Int. Ed. 45 2006 4305 4309
19. P.K. Koech, and M.J. Krische Tetrahedron 62 2006 10594 10602
20. M. Ito, A. Sakaguchi, C. Kobayashi, and T. Ikariya J. Am. Chem. Soc. 129 2007 290 291
21. J.F. Bower, T. Riis-Johannessen, P. Szeto, A.J. Whitehead, and T. Gallagher Chem. Commun. 2007 728 730
22. T. Nemoto, T. Sakamoto, T. Fukuyama, and Y. Hamada Tetrahedron Lett. 48 2007 4977 4981
23. P.S. Hynes, P.A. Stupple, and D.J. Dixon Org. Lett. 10 2008 1389 1391
24. G. Valero, J. Schimer, I. Cisarova, J. Vesely, A. Moyano, and R. Rios Tetrahedron Lett. 50 2009 1943 1946
25. M.-H. Kim, Y. Park, B.-S. Jeong, H.-G. Park, and S.-S. Jew Org. Lett. 12 2010 2826 2829
26. S. Cihalova, G. Valero, J. Schimer, M. Humpl, M. Dracinsky, A. Moyano, R. Rios, and J. Vesely Tetrahedron 67 2011 8942 8950
27. M.I. Lansdell, D. Hepworth, A. Calabrese, A.D. Brown, J. Blagg, D.J. Burring, P. Wilson, D. Fradet, T.B. Brown, F. Quinton, N. Mistry, K. Tang, N. Mount, P. Stacey, N. Edmunds, C. Adams, S. Gaboardi, S. Neal-Morgan, C. Wayman, S. Cole, J. Phipps, M. Lewis, H. Verrier, V. Gillon, N. Feeder, A. Heatherington, S. Sultana, S. Haughie, S.W. Martin, M. Sudworth, and S. Tweedy J. Med. Chem. 53 2010 3183 3197
28. C.L. Lynch, J.J. Hale, R.J. Budhu, A.L. Gentry, P.E. Finke, C.G. Caldwell, S.G. Mills, M. MacCoss, D.M. Shen, K.T. Chapman, L. Malkowitz, M.S. Springer, S.L. Gould, J.A. DeMartino, S.J. Siciliano, M.A. Cascieri, A. Carella, G. Carver, K. Holmes, W.A. Schleif, R. Danzeisen, D. Hazuda, J. Kessler, J. Lineberger, M. Miller, and E. Emini Org. Lett. 5 2003 2473 2475
29. J.R. Young, R. Eid, C. Turner, R.J. DeVita, M.M. Kurtz, K.-L.C. Tsao, G.G. Chicchi, A. Wheeldon, E. Carlson, and S.G. Mills Bioorg. Med. Chem. Lett. 17 2007 5310 5315
30. T. Yokosaka, T. Nemoto, and Y. Hamada Chem. Commun. 48 2012 5431 5433
31. For recent representative examples of ipso-Friedel-Crafts-type addition of phenol derivatives, see T. Nemoto, Y. Ishige, M. Yoshida, Y. Kohno, M. Kanematsu, and Y. Hamada Org. Lett. 12 2010 5020 5023
32. Q.-F. Wu, W.-B. Liu, C.-X. Zhuo, Z.-Q. Rong, K.-Y. Ye, and S.-L. You Angew. Chem., Int. Ed. 50 2011 4455 4458
33. S. Rousseaux, J. Garcia-Fortanet, M.A. Del Aguila Sanchez, and S.L. Buchwald J. Am. Chem. Soc. 133 2011 9282 9285
34. M. Yoshida, T. Nemoto, Z. Zhao, Y. Ishige, and Y. Hamada Tetrahedron: Asymmetry 23 2012 859 866
35. Q. Yin, and S.-L. You Org. Lett. 14 2012 3526 3529
36. H. Rodríguez-Solla, C. Concellón, P. Tuya, S. García-Granda, and M.R. Díaz Adv. Synth. Catal. 354 2012 295 300
37. C.-X. Zhuo, W. Zhang, and S.-L. You Angew. Chem., Int. Ed. 51 2012 12662 12686
38. For a review, see C. Olier, M. Kaafarani, S. Gastaldi, and M.P. Bertrand Tetrahedron 66 2010 413 445
39. For recent selected examples of aza-Prins reaction, see: A.P. Dobbs, S.J.J. Guesné, R.J. Parker, J. Skidmore, R.A. Stephenson, and M.B. Hursthouse Org. Biomol. Chem. 8 2010 1064 1080
40. J.S. Yadav, P. Borkar, P.P. Chakravarthy, B.V.S. Reddy, A.V.S. Sarma, S.J. Basha, B. Sridhar, and R. Gree J. Org. Chem. 75 2010 2081 2084
41. J.S. Yadav, B.V.S. Reddy, K. Ramesh, G.G.K.S.N. Kumar, and R. Gree Tetrahedron Lett. 51 2010 818 821
42. H. Kinoshita, O.J. Ingham, W.W. Ong, A.B. Beeler, and J.A. Porco Jr. J. Am. Chem. Soc. 132 2010 6412 6418
43. R.M. Carballo, G. Valdomir, M. Purino, V.S. Martín, and J.I. Padrón Eur. J. Org. Chem. 2010 2304 2313
44. B.V.S. Reddy, P. Borkar, P.P. Chakravarthy, J.S. Yadav, and R. Gree Tetrahedron Lett. 51 2010 3412 3416
45. E. Hasegawa, N. Hiroi, C. Osawa, E. Tayama, and H. Iwamoto Tetrahedron Lett. 51 2010 6535 6538
46. Y.W. Son, T.H. Kwon, J.K. Lee, A.N. Pae, J.Y. Lee, Y.S. Cho, and S.-J. Min Org. Lett. 13 2011 6500 6503
47. B.V.S. Reddy, P. Borkar, J.S. Yadav, B. Sridhar, and R. Gree J. Org. Chem. 76 2011 7677 7690
48. V. Parchinsky, A. Shumsky, and M. Krasavin Tetrahedron Lett. 52 2011 7157 7160
49. V. Parchinsky, A. Shumsky, and M. Krasavin Tetrahedron Lett. 52 2011 7161 7163
50. B.V.S. Reddy, K. Ramesh, A.V. Ganesh, G.G.K.S. N. Kumar, J.S. Yadav, and R. Gree Tetrahedron Lett. 52 2011 495 498
51. Q. Chen, X. Huo, Z. Yang, and X. She Chem. Asian J. 7 2012 2543 2546
52. X. Liu, M.P. McCormack, and S.P. Waters Org. Lett. 14 2012 5574 5577
53. B.V.S. Reddy, D.N. Chaya, J.S. Yadav, and R. Gree Synthesis 44 2012 297 303