1,3-Dipolar cycloadditions of N-benzyl-2,3-O-isopropylidene-D- glyceraldehyde nitrone to methoxyallene - Control of site- and diastereoselectivity of isoxazolidine formation by Lewis acids

European Journal of Organic Chemistry

Volumn , Issue 2, 2008, Pages 277-284

  Dugovič, Branislav ^a,b   Fišera, Lubor ^b   Reißig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

1,3 Dipolar cycloaddition; Isoxazolidines; Lewis acids; Methoxyallene; Nitrone

Indexed keywords

EID: 38349146735     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700724     Document Type: Article

References (88)

1. For reviews on 1,3-dipolar cycloadditions of nitrones see: a) J. J. Tufariello in 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), Wiley-Interscience, New York, 1984, vol. 2, chapter 9, pp. 83-168;
2. b) R. C. F. Jones, J. N. Martin in The Chemistry of Heterocyclic Compounds, vol. 59: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (Eds.: A. Padwa, W. H. Pearson), John Wiley & Sons, New York, 2002, chapter 1, pp. 1-81;
3. for reviews on nucleophilic additions to nitrones see: c) P. Merino, S. Franco, F. L. Merchán, T. Tejero, Synlett 2000, 442-454;
4. d) F. Cardona, A. Goti, Angew. Chem. 2005, 117, 8042-8045;
5. Angew. Chem. Int. Ed. 2005, 44, 7832-7835.
6. a) W. Schade, H.-U. Reißig, Synlett 1999, 632-634;
7. b) R. Pulz, S. Cicchi, A. Brandi, H.-U. Reißig, Eur. J. Org. Chem. 2003, 1153-1156;
8. c) M. Helms, W. Schade, R. Pulz, T. Watanabe, A. Al-Harrasi, L. Fišera, I. Hlobilová, G. Zahn, H.-U. Reißig, Eur. J. Org. Chem. 2005, 1003-1019.
9. a) R. Pulz, T. Watanabe, W. Schade, H.-U. Reißig, Synlett 2000, 983-986;
10. b) R. Pulz, A. Al-Harrasi, H.-U. Reißig, Synlett 2002, 817-819;
11. c) R. Pulz, A. Al-Harrasi, H.-U. Reißig, Org. Lett. 2002, 4, 2353-2355;
12. d) R. Pulz, W. Schade, H.-U. Reißig, Synlett 2003, 405-407;
13. e) M. Helms, H.-U. Reißig, Eur. J. Org. Chem. 2005, 998-1001;
14. f) A. Al-Harrasi, H.-U. Reißig, Synlett 2005, 1152-1154;
15. g) A. Al-Harrasi, H.-U. Reißig, Angew. Chem. Int. Ed. 2005, 44, 6227-6231;
16. Angew. Chem. 2005, 117, 6383-6387;
17. h) A. Al-Harrasi, H.-U. Reißig, Synlett 2005, 2376-2378;
18. i) F. Pfrengle, A. Al-Harrasi, H.-U. Reißig, Synlett 2006, 3498-3500;
19. j) B. Bressel, B. Egart, A. Al-Harrasi, R. Pulz, H.-U. Reißig, I. Brüdgam, Eur. J. Org. Chem. 2007, in press.
20. For the synthetic use of other 1,2-oxazine derivatives see: R. Zimmer, H.-U. Reißig, Angew. Chem. 1988, 100, 1576-1577;
21. Angew. Chem. Int. Ed. Engl. 1988, 27, 1518-1519;
22. H.-U. Reißig, C. Hippeli, T. Arnold, Chem. Ber. 1990, 123, 2403-2411 and references cited therein.
23. R. Huisgen, Angew. Chem. 1963, 75, 604-637;
24. Angew. Chem. Int. Ed. Engl. 1968, 7, 321-406.
25. a) M. Murakami, T. Matsuda in Modern Allene Chemistry (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004, vol. 2, chapter 12, pp. 727-815;
26. b) A. Padwa, W. H. Bullock, D. N. Kline, J. Perumattam, J. Org. Chem. 1989, 54, 2862-2869;
27. c) A. Padwa, M. Meske, Z. Ni, Tetrahedron Lett. 1993, 34, 5047-5050;
28. d) A. Piperno, A. Rescifina, A. Corsaro, M. A. Chiacchio, A. Procopio, R. Romeo, Eur. J. Org. Chem. 2007, 1517-1521;
29. e) G. Broggini, G. Zecchi, Gazz. Chim. Ital. 1996, 126, 479-488;
30. f) A. Padwa, M. Matzinger, Y. Tomioka, M. K. Venkatramanan, J. Org. Chem. 1988, 53, 955-963;
31. g) P. Parpani, G. Zecchi, J. Org. Chem. 1987, 52, 1417-1421;
32. h) W. R. Dolbier Jr, G. E. Wicks, C. R. Burkholder, J. Org. Chem. 1987, 52, 2196-2201.
33. a) K. V. Gothelf, S. Kanemasa, K. A. Jørgensen in Cycloaddition Reactions in Organic Synthesis (Eds.: S. Kobayashi, K. A. Jørgensen), Wiley-VCH, Weinheim, 2001, pp. 211-326;
34. b) K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863-909.
35. a) J.-P. G. Seerden, M. M. M. Kuypers, H. W. Scheeren, Tetrahedron: Asymmetry 1995, 6, 1441-1450;
36. b) J.-P. G. Seerden, M. M. M. Kuypers, H. W. Scheeren, Tetrahedron 1997, 53, 11843-11852;
37. c) M. J. Meske, J. Prakt. Chem. 1997, 339, 426-433;
38. d) K. B. Simonsen, P. Bayón, R. G. Hazell, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 1999, 121, 3845-3853;
39. e) K. B. Jensen, M. Roberson, K. A. Jørgensen, J. Org. Chem. 2000, 65, 9080-9084;
40. f) K. B. Simonsen, K. A. Jørgensen, Q. S. Hu, L. Pu, Chem. Commun. 1999, 811-812;
41. g) D. D. Dhavale, C. Trombini, J. Chem. Soc. Chem. Commun. 1992, 1268-1270.
42. B. Dugovič, T. Wiesenganger, L. Fišera, C. Hametner, N. Prónayová, Heterocycles 2005, 65, 591-605.
43. DFT calculations were carried out using B3LYP exchange-correlation functionals together with 6-31G* basis set implemented in software PC GAMESS version 6.5; a) M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem. 1993, 14, 1347-1363;
44. b) A. A. Granovsky, PC GAMESS version 6.5, http://classic.chem.msu.su/ gran/gamess/index.html.
45. L. R. Domingo, M. J. Aurell, P. Perez, R. Contreras, Tetrahedron 2002, 58, 4417-4423.
46. a) P. Perez, L. R. Domingo, M. Jose Aurell, R. Contreras, Tetrahedron 2003, 59, 3117-3125;
47. b) R. Herrera, A. Nagarajan, M. A. Morales, F. Mendez, H. A. Jimenez-Vazquez, L. G. Zepeda, J. Tamariz, J. Org. Chem. 2001, 66, 1252-1263;
48. c) L. R. Domingo, M. Arnó, P. Merino, T. Tejero, Eur. J. Org. Chem. 2006, 3464-3472;
49. d) L. R. Domingo, Eur. J. Org. Chem. 2000, 2265-2272;
50. e) L. R. Domingo, W. Benchouk, S. M. Mekelleche, Tetrahedron 2007, 63, 4464-4471.
51. a) P. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev. 2003, 103, 1793-1873;
52. b) D. H. Ess, G. O. Jones, K. N. Houk, Adv. Synth. Catal. 2006, 348, 2337-2361.
53. K. N. Houk, M. N. Paddon-Row, N. G. Rondan, Y. D. Wu, F. K. Brown, D. C. Spellmeyer, J. T. Metz, Y. Li, R. J. Loncharich, Science 1986, 231, 1108-1117.
54. a) A. Dondoni, S. Franco, F. Junquera, F. L. Merchán, P. Merino, T. Tejero, V. Bertolasi, Chem. Eur. J. 1995, 1, 505-520;
55. b) F. Degiorgis, M. Lombardo, C. Trombini, Tetrahedron 1997, 53, 11721-11730.
56. a) P. DeShong, M. Dicken, J. M. Leginus, R. R. Whittle, J. Am. Chem. Soc. 1984, 106, 5598-5602;
57. b) P. Merino, J. A. Mates, J. Revuelta, T. Tejero, U. Chiacchio, G. Romeo, D. Iannazzo, R. Romeo, Tetrahedron: Asymmetry 2002, 13, 173-190.
58. For a recent application of α-methylene-β-amino acid derivatives see: a) R. Galeazzi, G. Martelli, M. Orena, S. Rinaldi, P. Sabatino, Tetrahedron 2005, 61, 5465-5473;
59. b) D. Balan, H. Adolfsson, Tetrahedron Lett. 2004, 45, 3089-3092;
60. c) V. Declerck, P. Ribiere, J. Martinez, F. Lamaty, J. Org. Chem. 2004, 69, 8372-8381;
61. d) H.-Y. Chen, L. N. Patkar, S.-H. Ueng, C.-C. Lin, A. S.-Y. Lee, Synlett 2005, 2035-2038;
62. e) J. Barluenga, B. Baragana, J. M. Concellón, J. Org. Chem. 1999, 64, 2843-2846.
63. For recent advances on the aza-Morita-Baylis-Hillman reaction see: a) K. Matsui, S. Takizawa, H. Sasai, J. Am. Chem. Soc. 2005, 127, 3680-3681;
64. b) D. Balan, H. Adolfsson, J. Org. Chem. 2001, 66, 6498-6501;
65. c) M. Shi, L.-H. Chen, Chem. Commun. 2003, 1310-1311;
66. d) M. Shi, Y.-M. Xu, Y.-L. Shi, Chem. Eur. J. 2005, 11, 1794-1802;
67. e) G. Masson, C. Housseman, J. Zhu, Angew. Chem. 2007, 119, 4698-4712;
68. Angew. Chem. Int. Ed. 2007, 46, 4614-4628.
69. For alternatives towards aza-Morita-Baylis-Hillman products see: a) Y. Génisson, C. Massardier, I. Gautier-Luneau, A. E. Greene, J. Chem. Soc. Perkin Trans. 1 1996, 2869-2872;
70. b) D. Bierbaum, D. Seebach, Aust. J. Chem. 2004, 57, 859-863;
71. c) W. Adam, H.-G. Degen, O. Krebs, C. R. Saha-Möller, J. Am. Chem. Soc. 2002, 124, 12938-12939;
72. d) T. Akiyama, K. Daidouji, K. Fuchibe, Org. Lett. 2003, 5, 3691-3693;
73. e) M. A. Loreto, A. Migliorini, P. A. Tardella, J. Org. Chem. 2006, 71, 2163-2166.
74. a) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates, VCH Publishers, New York, 1988;
75. b) I. Blanáriková-Hlobilová, Z. Kopanič áková, L. Fišera, M. K. Cyrański, P. Salanski, J. Jurczak, N. Prónayová, Tetrahedron 2003, 59, 3333-3339;
76. c) J. Kubáň, A. Kolarovič, L. Fišera, V. Jäger, O. Humpa, N. Prónayová, Synlett 2001, 1866-1868.
77. a) S.-I. Murahashi, Y. Kodera, T. Hosomi, Tetrahedron Lett. 1988, 29, 5949-5952;
78. b) P. Bayón, P. March, M. Figueredo, J. Font, Tetrahedron 1998, 54, 15691-15700;
79. c) C. Chevrier, A. Defoin, Synthesis 2003, 1221-1224;
80. d) F. Machetti, F. M. Cordero, F. De Sarlo, A. Brandi, Tetrahedron 2001, 57, 4995-4998.
81. For discussion of the possible mechanism see: a) R. P. Rebman, N. H. Cromwell, Tetrahedron Lett. 1965, 6, 4833-4836;
82. b) N. H. Cromwell, R. P. Rebman, J. Org. Chem. 1967, 32, 3830-3833;
83. c) M. C. Eagen, N. H. Cromwell, J. Org. Chem. 1974, 39, 3863-3866.
84. Reaction conditions were not optimized. There was no complete conversion of isoxazolidines 4a and 4c, respectively. Under these conditions 14% of 4a and 42% of 4c were recovered.
85. A. Dondoni, S. Franco, F. Junquera, F. Merchan, P. Merino, T. Tejero, Synth. Commun. 1994, 24, 2537-2550.
86. a) W. Reppe, Justus Liebigs Ann. Chem. 1955, 596, 1-158;
87. b) F. J. Weiberth, S. S. Hall, J. Org. Chem. 1985, 50, 5308-5314.
88. C. D. Beard, K. Baum, J. Org. Chem. 1974, 39, 3875-3877.