Boc-protected amines via a mild and efficient one-pot curtius rearrangement

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4107-4110

  Lebel, Hélène ^a   Leogane, Olivier ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1 ADAMANTANEACETIC ACID; 1-ADAMANTANEACETIC ACID; ACETIC ACID DERIVATIVE; ADAMANTANE; AMINE; DRUG DERIVATIVE; MALONIC ACID; MALONIC ACID DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY;

ACETIC ACIDS; ADAMANTANE; AMINES; CATALYSIS; MALONATES; MOLECULAR STRUCTURE; SUBSTRATE SPECIFICITY; ZINC;

EID: 25444499204     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051428b     Document Type: Article

References (94)

1. (a) Smith, P. A. S. Org. React. 1946, 3, 337-349.
2. (b) Shioiri, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p 795.
3. (c) Scriven, E. F.; Turnbull, K. Chem. Rev. 1988, 88, 297-368.
4. Selected examples: (a) Jean, L.; Baglin, I.; Rouden, J.; Maddaluno, J.; Lasne, M. C. Tetrahedron Lett. 2001, 42, 5645-5649.
5. (b) Nettekoven, M. Synlett 2001, 1917-1920.
6. (c) Macor, J. E.; Mullen, G.; Verhoest, P.; Sampognaro, A.; Shepardson, B.; Mack, R. A. J. Org. Chem. 2004, 69, 6493-6495.
7. Selected examples: (a) Washburne, S. S.; Peterson, W. R., Jr. Synth. Commun. 1972, 2, 227-230.
8. (b) Van Reijendam, J. W.; Baardman, F. Synthesis 1973, 413-414.
9. (c) Brandstrom, A.; Lamm, B.; Palmertz, I. Acta Chem. Scand. 1974, 28, 699-701.
10. (d) Erhardt, P. W. J. Org. Chem. 1979, 44, 883-884.
11. (e) Warren, J. D.; Press: J. B. Synth. Commun. 1980, 10, 107-110.
12. (f) Pfister, J. R.; Wymann, W. E. Synthesis 1983, 38-40.
13. (g) Lo Scalzo, R.; Mascitelli, L.; Scarpati, M. L. Gazz. Chim. Ital. 1988, 118, 819-820.
14. (h) Khoukhi, M.; Vaultier, M.; Benalil, A.; Carboni, B. Synthesis 1996, 483-487.
15. (i) Govindan, C. K. Org. Proc. Res. Dev. 2002, 6, 74-77.
16. (j) Kende, A. S.; Lan, J.; Arad, D. Tetrahedron Lett. 2002, 43, 5237-5239.
17. (k) Patil, B. S.; Vasanthakumar, G.-R.; Babu, V. V. S. J. Org. Chem. 2003, 68, 7274-7280.
18. Selected examples: (a) Weinstock, J. J. Org. Chem. 1961, 26, 3511.
19. (b) Overman, L. E.; Taylor, G. F.; Petty, C. B.; Jessup, P. J. J. Org. Chem. 1978, 43, 2164-2167.
20. (c) Kaiser, C.; Weinstock, J. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 910.
21. (d) Guichard, G.; Semetey, V.; Rodriguez, M.; Briand, J.-P. Tetrahedron Lett. 2000, 41, 1553-1557.
22. (e) Remen, L.; Vasella, A. Helv. Chim. Acta 2002, 85, 1118-1127.
23. (f) Kuramochi, K.; Osada, Y.; Kitahara, T. Tetrahedron 2003, 59, 9447-9454.
24. (g) England, E. A.; Gopi, H. N.; Appella, D. H. Org. Lett. 2004, 6, 213-215.
25. (h) Boeckman, R. K., Jr.; Reeder, L. M. Synlett 2004, 1399-1403.
26. (i) Dussault, P. H.; Xu, C. Tetrahedron Lett. 2004, 45, 7455-7457.
27. Alternative methods: (a) Lee, J. G.; Kwak, K. H. Tetrahedron Lett. 1992, 33, 3165-3166 .
28. (b) Froyen, P. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 89, 57-61.
29. (c) Rawal, V. H.; Zhong, H. M. Tetrahedron Lett. 1994, 35, 4947-4950 .
30. (d) Elmorsy, S. S. Tetrahedron Lett. 1995, 36, 1341-1342.
31. (e) Gumaste, V. K.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron Lett. 2002, 43, 1345-1346.
32. (f) Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2002, 43, 3413-3414.
33. (g) Tale, R. H.; Patil, K. M. Tetrahedron Lett. 2002, 43, 9715-9716.
34. (h) Bose, D. S.; Reddy, A. V. N. Tetrahedron Lett. 2003, 44, 3543-3545.
35. (i) Bao, W. L.; Wang, Q. A. J. Chem. Res., Synop. 2003, 700-701.
36. (a) Ende, D. J. a.; DeVries, K. M.; Clifford, P. J.; Brenek, S. J. Org. Proc. Res. Dev. 1998, 2, 382-392.
37. (b) Nettekoven, M.; Jenny, C. Org. Proc. Res. Dev. 2003, 7, 38-43.
38. Affandi, H.; Bayquen, A. V.; Read, R. W. Tetrahedron Lett. 1994, 35, 2729-2732.
39. (a) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203-6205 .
40. (b) Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151-2157.
41. (c) Murato, K.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull. 1975, 23, 1738-1740.
42. (d) Capson, T. L.; Poulter, C. D. Tetrahedron Lett 1984, 25, 3515-3518.
43. (e) Wolff, O.; Waldvogel, S. R. Synthesis 2004, 1303-1305.
44. Selected recent examples: (a) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009-6016.
45. (b) Migawa, M. T.; Swayze, E. E. Org. Lett. 2000, 2, 3309-3311.
46. (c) Roers, R.; Verdine, G. L. Tetrahedron Lett. 2001, 42, 3563-3565.
47. (d) Beria, I.; Nesi, M. Tetrahedron Lett. 2002, 43, 7323-7327.
48. (e) Sasmal, S.; Geyer, A.; Maier, M. E. J. Org. Chem. 2002, 67, 6260-6263.
49. (f) Ecija, M.; Diez, A.; Rubiralta, M.; Casamitjana, N.; Kogan, M. J.; Giralt, E. J. Org. Chem. 2003, 68, 9541-9553.
50. (g) Goeksu, S.; Kazaz, C.; Suetbeyaz, Y.; Secen, H. Helv. Chim. Acta 2003, 86, 3310-3313.
51. (h) Hakogi, T.; Taichi, M.; Katsumura, S. Org. Lett. 2003, 5, 2801-2804.
52. (i) Kambourakis, S.; Rozzell, J. D. Adv. Synth. Catal. 2003, 345, 699-705.
53. (j) Spino, C.; Gobdout, C. J. Am. Chem. Soc. 2003, 125, 12106-12107.
54. (k) Wipf, P.; Pierce, J. G.; Wang, X. Tetrahedron: Asymmetry 2003, 14, 3605-3611.
55. (l) Chien, T.-C.; Meade, E. A.; Hinkley, J. M.; Townsend, L. B. Org. Lett. 2004, 6, 2857-2859.
56. (m) Doussineau, T.; Durand, J. O.; Granier, M.; Smaihi, M.; Valtchev, V. Synlett 2004, 1735-1738.
57. (n) Gomez-Sanchez, E.; Marco-Contelles, J. Tetrahedron 2005, 61, 1207-1219.
58. Alternative procedures using solid-phase synthesis: (a) Richter, L. S.; Andersen, S. Tetrahedron Lett. 1998, 39, 8747-8750.
59. (b) Sunami, S.; Sagara, T.; Ohkubo, M.; Morishima, H. Tetrahedron Lett. 1999, 40, 1721-1724.
60. (c) Lu, Y.; Taylor, R. T. Tetrahedron Lett. 2003, 44, 9267-9269.
61. (a) Carpino, L. A.; Carpino, B. A.; Crowley, P. J.; Giza, C. A.; Terry, P. H. Org. Synth. 1973, 5, 157-159.
62. (b) Yajima, H.; Kawatani, H. Chem. Pharm. Bull. 1968, 16, 182-184.
63. (c) Dean, C. S.; Tarbell, D. S.; Friederang, A. W. J. Org. Chem. 1970, 35, 3393-3397.
64. (d) Anselme, J. P.; Sakai, K. J. Org. Chem. 1971, 36, 2387-2388.
65. (e) Insalaco, M. A.; Tarbell, D. S. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 207.
66. (a) Newman, M. S.; Gildenhorn, H. L. J. Am. Chem. Soc. 1948, 70, 317-319.
67. (b) Coleman, R. A.; Newman, M. S.; Garrett, A. B. J. Am. Chem. Soc. 1954, 76, 4534-4538.
68. (c) Prakash, G. K. S.; Iyer, P. S.; Arvanaghi, M.; Olah, G. A. J. Org. Chem. 1983, 48, 3358-3359.
69. (d) Farooq, O.; Wang, Q.; Wu, A. H.; Olah, G. A. J. Org. Chem. 1990, 55, 4282-4283.
70. (a) Otera, J.; Yano, T.; Okawara, R. Organometallics 1986, 5, 1167-1170.
71. (b) Duggan, M. E.; Imagire, J. S. Synthesis 1989, 131-132.
72. (c) Houghton, R. P.; Rice, C. R. Chem. Commun. 1995, 2265-2266.
73. (d) Houghton, R. P.; Mulvaney, A. W. J. Organomet. Chem. 1996, 518, 21-27.
74. (e) Houghton, R. P.; Mulvaney, A. W. J. Organomet. Chem. 1996, 517, 107-113.
75. (f) Ligabue, R. A.; Monteiro, A. L.; de Souza, R. F.; de Souza, M. O. J. Mol. Catal. A-Chem. 1998, 130, 101-105.
76. (g) Ligabue, R. A.; Monteiro, A. L.; de Souza, R. F.; de Souza, M. O. J. Mol. Catal. A-Chem. 2000, 157, 73-78.
77. 2), and only 33% of carbamate 9 was isolated.
78. 2. However, carbamate 11 was obtained with only 20% yield.
79. The enantiomeric excess was determined by supercritical-fluid chromatography (SFC) using a Chiracel OD, and a difference of 1% ee is within the experimental error.
80. Selected examples: (a) Ninomiya, K.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull. 1974, 22, 1398-1404.
81. (b) Koskinen, A. M. P.; Munoz, L. J. Org. Chem. 1993, 58, 879-886.
82. (c) Burgess, K.; Lim, D.; Ho, K. K.; Ke, C. Y. J. Org. Chem. 1994, 59, 2179-2185.
83. (d) Dekimpe, N.; Boeykens, M.; Tehrani, K. A. J. Org. Chem. 1994, 59, 8215-8219.
84. (e) Li, K. Q.; Du, W. S.; Que, N. L. S.; Liu, H. W. J. Am. Chem. Soc. 1996, 118, 8763-8764.
85. (f) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1-15.
86. (g) Nemes, C.; Jeannin, L.; Sapi, J.; Laronze, M.; Seghir, H.; Auge, F.; Laronze, J.-Y. Tetrahedron 2000, 56, 5479-5492.
87. (h) Sibi, M. P.; Deshpande, P. K. J. Chem. Soc., Perkin Trans. 1 2000, 1461-1466.
88. (i) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Tetrahedron 2001, 57, 2781-2786.
89. (j) Cochard, F.; Laronze, M.; Prost, E.; Nuzillard, J.-M.; Auge, F.; Petermann, C.; Sigaut, P.; Sapi, J.; Laronze, J.-Y. Eur. J. Org. Chem. 2002, 3481-3490.
90. (k) Bolm, C.; Schiffers, I.; Atodiresei, I.; Hackenberger, C. P. R. Tetrahedron: Asymmetry 2003, 14, 3455-3467.
91. (l) Kedrowski, B. L. J. Org. Chem. 2003, 68, 5403-5406.
92. (m) Larionov, O. V.; Kozhushkov, S. I.; de Meijere, A. Synthesis 2005, 158-160.
93. (n) Oba, M.; Tanaka, M.; Takano, Y.; Suemune, H. Tetrahedron 2005, 61, 593-598.
94. Fujita, T.; Adachi, K.; Kohara, T.; Kiuchi, M.; Chiba, K.; Teshima, K.; Mishina, T. U.S. 1999, 88pp., Cont.-int-part of Appl. No. PCT/JP95/ 01654. CODEN: USXXAM US5948820.