Applications and limitations of the I2-mediated carbamate annulation for the synthesis of piperidines: Five-versus six-membered ring formation

Journal of Organic Chemistry

Volumn 78, Issue 19, 2013, Pages 9791-9802

  Corkran, Hilary M ^a,b   Munneke, Stefan ^a   Dangerfield, Emma M ^a,b   Stocker, Bridget L ^a,b   Timmer, Mattie S M ^a  

^a VICTORIA UNIVERSITY OF WELLINGTON   (New Zealand)

^b MALAGHAN INSTITUTE OF MEDICAL RESEARCH   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ANNULATION PRODUCTS; CHIRAL SCAFFOLDS; D-GALACTOSE; D-GLUCOSE; PYRROLIDINES; SIX-MEMBERED RINGS; SYNTHETIC STRATEGIES;

ALKALOIDS; AROMATIC COMPOUNDS; ORGANIC POLLUTANTS; SCAFFOLDS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

CARBAMIC ACID DERIVATIVE; DEOXYGLUCOSE; GALACTOSE; IODINE; PIPERIDINE DERIVATIVE; 1 DEOXYNOJIRIMYCIN; 1-DEOXYGALACTONOJIRIMYCIN; DRUG DERIVATIVE; FAGOMINE; FUCOSE; IMINOSUGAR; MIGALASTAT; PIPERIDINE;

AMINATION; ANNULATION REACTION; ARTICLE; CYCLIZATION; HYDROLYSIS; ISOMER; STEREOCHEMISTRY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

1-DEOXYNOJIRIMYCIN; CARBAMATES; CYCLIZATION; FUCOSE; IMINO PYRANOSES; MOLECULAR STRUCTURE; PIPERIDINES; STEREOISOMERISM;

EID: 84885102872     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401512h     Document Type: Article

References (78)

1. Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645-1680
2. Butters, T. D.; Dwek, R. A.; Platt, F. M. Curr. Top. Med. Chem. 2003, 3, 561-574
3. Greimel, P.; Spreitz, J.; Stütz, A. E.; Wrodnigg, T. M. Curr. Top. Med. Chem. 2003, 3, 513-523
4. Borges de Melo, E.; da Silveira Gomes, A.; Carvalho, I. Tetrahedron 2006, 62, 10277-10302
5. Merino, P.; Delso, I.; Marca, E.; Tejero, T.; Matute, R. Curr. Chem. Biol. 2009, 3, 253-271
6. Nash, R. J.; Kato, A.; Yu, C.-Y.; Fleet, G. W. J. Future Med. Chem 2011, 3, 1513-1521
7. Lopez, O.; Merino-Montiel, P.; Martos, S.; Gonzalez-Benjumea, A. Carbohydr. Chem. 2012, 38, 215-262
8. Alonzi, D. S.; Butters, T. D. Chimia 2011, 65, 35-39
9. Iminosugars: From Synthesis to Therapeutic Applications; Compain, P.; Martin, O. R., Eds.; Wiley: Chichester, U.K., 2007.
10. Segal, P.; Feig, P. U.; Schernthaner, G.; Ratzmann, K. P.; Rybka, J.; Petzinna, D.; Berlin, C. Diabetes Care 1997, 20, 687-691
11. See: A Study of AT1001 in Patients with Fabry Disease. http://www.clinicaltrials.gov/ct/gui/show/NCT00231036 (accessed July 7, 2013).
12. Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515-554
13. Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952
14. Kato, A.; Asano, N.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. J. Nat. Prod. 1997, 60, 312-314
15. Nojima, H.; Kimura, I.; Chen, F.-J.; Sugihara, Y.; Haruno, M.; Kato, A.; Asano, N. J. Nat. Prod. 1998, 61, 397-400
16. Fan, J.-Q.; Ishii, S.; Asano, N.; Suzuki, Y. Nat. Med. 1999, 5, 112-115
17. Dangerfield, E. M.; Timmer, M. S. M.; Stocker, B. L. Org. Lett. 2009, 11, 535-538
18. Dangerfield, E. M.; Gulab, S. A.; Plunkett, C. H.; Timmer, M. S. M.; Stocker, B. L. Carbohydr. Res. 2010, 345, 1360-1365
19. Dangerfield, E. M.; Plunkett, C. H.; Stocker, B. L.; Timmer, M. S. M. Molecules 2009, 14, 5298-5307
20. Pearson, M. S. M.; Mathé-Allainmat, M.; Fargeas, V.; Lebreton, J. Eur. J. Org. Chem. 2005, 2159-2191
21. Afarinkia, K.; Bahar, A. Tetrahedron: Asymmetry 2005, 16, 1239-1287
22. Davis, B. G. Tetrahedron: Asymmetry 2009, 20, 652-671
23. Stocker, B. L.; Dangerfield, E. M.; Win-Mason, A. L.; Haslett, G. W.; Timmer, M. S. M. Eur. J. Org. Chem. 2010, 1615-1637
24. Wijdeven, M. A.; Willemsen, J.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2010, 2831-2844
25. Dangerfield, E. M.; Plunkett, C. H.; Win-Mason, A. L.; Stocker, B. L.; Timmer, M. S. M. J. Org. Chem. 2010, 75, 5470-5477
26. Timmer, M. S. M.; Dangerfield, E. M.; Cheng, J. M. H.; Gulab, S. A.; Stocker, B. L. Tetrahedron Lett. 2011, 52, 4803-4805
27. Miriyala, B.; Bhattacharyya, S.; Williamson, J. S. Tetrahedron 2004, 60, 1463-1471
28. Pelter, A.; Rosser, R. M.; Mills, S. J. Chem. Soc., Perkin Trans. 1 1984, 717-720
29. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897-2904
30. Gomez, S.; Peters, J. A.; van der Waal, J. C.; van den Brink, P. J.; Maschmeyer, T. Appl. Catal., A 2004, 261, 119-125
31. Gomez, S.; Peters, J. A.; Maschmeyer, T. Adv. Synth. Catal. 2002, 344, 1037-1057
32. Baxter, E.; Reitz, A. Org. React. 2002, 59, 1-714
33. McGhee, W.; Riley, D.; Christ, K.; Pan, Y.; Parnas, B. J. Org. Chem. 1995, 60, 2820-2830
34. Hampe, E. M.; Rudkevich, D. M. Tetrahedron 2003, 59, 9619-9625
35. Chmielewski, M. K. Tetrahedron Lett. 2012, 53, 666-669
36. Li, Y.; Roy, B.; Liu, X. Chem. Commun. 2011, 47, 8952-8954
37. Codée, J. D. C.; Ali, A.; Overkleeft, H. S.; van der Marel, G. A. C. R. Chim. 2011, 14, 178-193
38. Hagen, V.; Kilic, F.; Schaal, J.; Dekowski, B.; Schmidt, R.; Kotzur, N. J. Org. Chem. 2010, 75, 2790-2797
39. Ali, A.; Van den Berg, R. J. B. H. N.; Overkleeft, H. S.; Filippov, D. V.; van der Marel, G. A.; Codée, J. D. C. Tetrahedron Lett. 2009, 50, 2185-2188
40. Timmer, M. S. M.; Stocker, B. L.; Northcote, P. T.; Burkett, B. A. Tetrahedron Lett. 2009, 50, 7199-7204
41. Foster, A. B.; Overend, W. G.; Stacey, M.; Vaughan, G. J. Chem. Soc. 1954, 3367-3377
42. Toyokuni, T.; Cai, S.; Dean, B. Synthesis 1992, 1236-1238
43. Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701-3706
44. Heiker, F.-R.; Schueller, A. M. Carbohydr. Res. 1990, 203, 314-318
45. Takahata, H.; Banba, Y.; Ouchi, H.; Nemoto, H.; Kato, A.; Adachi, I. J. Org. Chem. 2003, 68, 3603-3607
46. van den Berg, R. J. B. H. N.; Wennekes, T.; Ghisaidoobe, A.; Donker-Koopman, W. E.; Strijland, A.; Boot, R. G.; van der Marel, G. A.; Aerts, J. M. F. G.; Overkleeft, H. S. ACS Med. Chem. Lett. 2011, 2, 519-522
47. Kumari, N.; Reddy, B. G.; Vankar, Y. D. Eur. J. Org. Chem. 2009, 160-169
48. Yorimitsu, H.; Murakami, Y.; Takamatsu, H.; Nishimura, S.; Nakamura, E. Chem.-Asian J. 2007, 2, 57-65
49. Skaanderup, P. R.; Poulsen, C. S.; Hyldtoft, L.; Jorgensen, M. R.; Madsen, R. Synthesis 2002, 1721-1727
50. Swamy, N. K.; Pyne, S. G. Synth. Commun. 2011, 41, 2435-2445
51. Bates, R. W.; Ng, P. S. Tetrahedron Lett. 2011, 52, 2969-2971
52. Jiangseubchatveera, N.; Bouillon, M. E.; Liawruangrath, B.; Liawruangrath, S.; Nash, R. J.; Pyne, S. G. Org. Biomol. Chem. 2013, 11, 3826-3833
53. Lombardo, M.; Morganti, S.; Trombini, C. J. Org. Chem. 2003, 68, 997-1006
54. Dana, G.; Danechpajouh, H. Bull. Soc. Chim. Fr. 1980, 395-399
55. Bock, M.; Buntin, K.; Müller, R.; Kirschning, A. Angew. Chem., Int. Ed. 2008, 47, 2308-2311
56. Stocker, B. L.; Win-Mason, A. L.; Timmer, M. S. M. Carbohydr. Res. 2012, 356, 163-171
57. Chamberlin, A. R.; Mulholland, R. L., Jr.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672-677
58. Song, W.-J.; Suh, D.-Y.; Kang, Y.-H.; No, K.; Han, B. H. Bull. Korean Chem. Soc. 1998, 19, 593-595
59. Ohta, H.; Sakata, Y.; Takeuchi, T.; Ishii, Y. Chem. Lett. 1990, 733-736
60. Masuda, H.; Takase, K.; Nishio, M.; Hasegawa, A.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1994, 59, 5550-5555
61. Giese, B.; Bartmann, D. Tetrahedron Lett. 1985, 26, 1197-1200
62. Chamberlin, A. R.; Dezube, M.; Dussault, P.; McMills, M. C. J. Am. Chem. Soc. 1983, 105, 5819-5825
63. Chamberlin, A. R.; Mulholland, R. L., Jr. Tetrahedron 1984, 40, 2297-2302
64. Midland, M. M.; Halterman, R. L. J. Org. Chem. 1981, 46, 1227-1229
65. Peeters, A.; Ameloot, R.; De Vos, D. E. Green Chem. 2013, 15, 1550-1557
66. Payne, G. B. J. Org. Chem. 1962, 27, 3819-3822
67. Hanson, R. M. Org. React. 2002, 60, 1-156
68. Winstein, S.; Goodman, L. J. Am. Chem. Soc. 1954, 76, 4373-4378
69. Lindgren, B. O.; Svahn, C. M. Acta Chem. Scand. 1970, 24, 2699-2704
70. Ganem, B. J. Am. Chem. Soc. 1976, 98, 858-859
71. Santelli, M.; Viala, J. Tetrahedron Lett. 1977, 18, 4397-4400
72. Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis 1988, 862-868
73. Brunel, Y.; Roussseau, G. Synlett 1995, 323-324
74. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736
75. Wipf, P.; Stephenson, C. R. J.; Walczak, M. A. A. Org. Lett. 2004, 6, 3009-3012
76. Win-Mason, A. L.; Dangerfield, E. M.; Tyler, P. C.; Stocker, B. L.; Timmer, M. S. M. Eur. J. Org. Chem. 2011, 4008-4014
77. Win-Mason, A. L.; Jongkees, S. A. K.; Withers, S. G.; Tyler, P. C.; Timmer, M. S. M.; Stocker, B. L. J. Org. Chem. 2011, 76, 9611-9621
78. Durette, P. L. Synthesis 1980, 1037-1038