Dehydrogenative TEMPO-Mediated Formation of Unstable Nitrones: Easy Access to N-Carbamoyl Isoxazolines

Chemistry - A European Journal

Volumn 21, Issue 34, 2015, Pages 12053-12060

  Gini, Andrea ^a,b   Segler, Marwin ^c   Kellner, Dominik ^a,b   Mancheño, Olga García ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

cycloadditon; dehydrogenative; isoxazolines; TEMPO; unstable N acyl nitrones

Indexed keywords

BIOACTIVITY; CONDENSATION REACTIONS;

CYCLOADDITON; DEHYDROGENATIVE; ISOXAZOLINES; NITRONES; TEMPO;

CYCLIZATION;

EID: 84938739630     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201501314     Document Type: Article

References (69)

1. Selected reviews
2. T. M. V. D. Pinho e Melo, Eur. J. Org. Chem. 2010, 3363-3376
3. P. Grünanger, P. Vita-Finzi, Isoxazolines, in The Chemistry of Heterocyclic Compounds, Vol. 49, (Eds.:, E. C. Taylor, A. Weissberger,), John Wiley & Sons, 1991, (Chapter 2) pp. 416-647.
4. A. G. Habeeb, P. N. Praveen Rao, E. E. Knaus, J. Med. Chem. 2001, 44, 2921-2927
5. M. E. Frakey, R. M. Garbaccio, G. D. Hartman, PCT Int. Appl. WO2006/023440, 43, 2006.
6. Representative example:, P. Aschwanden, L. Kværnø, R. W. Geisser, F. Kleinbeck, E. M. Carreira, Org. Lett. 2005, 7, 5741-5742.
7. A. Sakakura, M. Hori, M. Fushimi, K. Ishihara, J. Am. Chem. Soc. 2010, 132, 15550
8. M. M.-C. Lo, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 4572-4573
9. F. M. Cordero, F. Pisaneschi, A. Goti, J. Ollivier, J. Salaün, A. Brandi, J. Am. Chem. Soc. 2000, 122, 8075-8076
10. D. A. Evans, F. Kelibeck, M. Rueping, in Asymmetric Synthesis-The Essentials, (Eds.:, M. Christmann, S. Bräse,), Wiley-VCH, Weinheim, 2007, pp. 72, and references therein.
11. See, for example:, N. Wada, K. Kaneko, Y. Ukaji, K. Inomata, Chem. Lett. 2011, 40, 440-443, and referenced cited therein.
12. A. Brandi, F. Cardona, S. Cicchi, F. M. Cordero, A. Goti, Chem. Eur. J. 2009, 15, 7808-7821
13. H. Wei, C. Qiao, G. Liu, Z. Yang, C. Li, Angew. Chem. Int. Ed. 2013, 52, 620-624
14. Angew. Chem. 2013, 125, 648-652, and references therein.
15. I. A. Grigor′ev, in Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis: Novel Strategies in Synthesis (Ed.:, H. Feuer,), John Wiley & Sons Inc., New Jersey, 2008 (2 nd Ed.), (Chapter 2) pp. 129-434
16. P. Merino, in Science of Synthesis Vol. 27, (Ed., A. Padwa,), Thieme, Stuttgart, 2004, pp. 511-580
17. R. Bloch, Chem. Rev. 1998, 98, 1407-1438. See also
18. F. Cardona, A. Goti, Angew. Chem. Int. Ed. 2005, 44, 7832-7835
19. Angew. Chem. 2005, 117, 8042-8045.
20. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; (Eds.:, A. Padwa, W. H. Pearson,), Wiley: New York, 2002
21. K. V. Gothelf, K. A. Jørgensen, Chem. Commun. 2000, 1449-1458
22. K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863-909. See also
23. R. Huisgen, J. Org. Chem. 1976, 41, 403-419.
24. For stable N-protected nitrones, such as benzyl, allyl, or glycosyl, see
25. P. N. Confalone, G. Pizzolato, D. L. Confalone, M. R. Uskokovic, J. Am. Chem. Soc. 1980, 102, 1954-1960
26. K. Ben Ayed, A. Beauchard, J.-F. Poisson, S. Py, M. Y. Laurent, A. Martel, H. Ammar, S. Abid, G. Dujardin, Eur. J. Org. Chem. 2014, 2924-2932
27. A. Vaseila, R. Voeffray, Helv. Chim. Acta 1982, 65, 1953-1964
28. S. Cicchi, M. Marradi, M. Corsi, C. Faggi, A. Goti, Eur. J. Org. Chem. 2003, 4152-4161.
29. X. Guinchard, Y. Vallée, J.-N. Denis, Org. Lett. 2005, 7, 5147-5150
30. C. Gioia, F. Fini, A. Mazzanti, L. Bernardi, A. Ricci, J. Am. Chem. Soc. 2009, 131, 9614-9615.
31. K. M. Partridge, M. E. Anzovino, T. P. Yoon, J. Am. Chem. Soc. 2008, 130, 2920-2921
32. N. Morita, R. Kono, K. Fukui, A. Miyazawa, H. Masu, I. Azumaya, S. Ban, Y. Hashimoto, I. Okamoto, O. Tamura, J. Org. Chem. 2015, 80, 4797-4802.
33. An isolated early example using Ag2O as the oxidant
34. S. A. Hussain, A. H. Sharma, M. J. Perkins, D. Griller, Chem. Commun. 1979, 289-291. For a photocatalytic approach for stable N-aryl nitrones, see
35. H. Hou, S. Zhu, F. Pan, M. Rueping, Org. Lett. 2014, 16, 2872-2875.
36. For our previous contributions, see
37. H. Richter, O. García Mancheño, Org. Lett. 2011, 13, 6066-6069
38. H. Richter, R. Fröhlich, C. G. Daniliuc, O. García Mancheño, Angew. Chem. Int. Ed. 2012, 51, 8656-8660
39. Angew. Chem. 2012, 124, 8784-8788
40. R. Rohlmann, T. Stopka, H. Richter, O. García Mancheño, J. Org. Chem. 2013, 78, 6050-6064, and references therein.
41. Selected reviews on dehydrogenative coupling reactions
42. C.-J. Li, Acc. Chem. Res. 2009, 42, 335-344
43. C. J. Scheuermann, Chem. Asian J. 2009, 4, 436-451
44. M. Klussmann, D. Sureshkumar, Synthesis 2011, 353-369
45. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780-1824
46. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215-1292
47. R. Rohlmann, O. García Mancheño, Synlett 2013, 24, 6-10.
48. For the oxidation of hydroxylamines to nitrones with TEMPO, see
49. S. Murarka, A. Studer, Adv. Synth. Catal. 2011, 353, 2708-2714
50. P. Merino, I. Delso, T. Tejero, F. Cardona, A. Goti, Synlett 2007, 2651-2654.
51. Selected reviews on TEMPO chemistry
52. T. Stopka, O. García Mancheño, Synthesis 2013, 45, 1602-1611
53. L. Tebben, A. Studer, Angew. Chem. Int. Ed. 2011, 50, 5034-5068
54. Angew. Chem. 2011, 123, 5138-5174
55. T. Vogler, A. Studer, Synthesis 2008, 1979-1993
56. R. A. Sheldon, I. W. C. E. Arends, Adv. Synth. Catal. 2004, 346, 1051-1071.
57. The use of DCE at 70°C provided similar results (80 vs. 87% yield).
58. Unfortunately, the extension to nonactivated dipolarophiles such as styrene was not possible using DMAD as a cheap sacrificial reagent.
59. B. König, W. Pitsch, M. Kleon, R. Vasold, M. Prall, P. R. Schreiner, J. Org. Chem. 2001, 66, 1742-1746.
60. Electron-withdrawing groups at the nitrogen lower the energy of the HOMO, which affects the HOMOnitrone-LUMOdipolarophile interaction. See: Molecular Orbitals and Organic Chemical Reactions: Reference Edition, (Ed.:, I. Fleming,), Wiley-VCH, 2010.
61. For the reaction of isolated N-Bn nitrone 8 with DMAD, see:, N. Coçkun, A. Öztürk, Tetrahedron 2006, 62, 12057-12063.
62. K. U. Ingold, K. Adamic, D. F. Bowman, T. Gillan, J. Am. Chem. Soc. 1971, 93, 902-908
63. D. F. Bowman, J. Brokenshire, T. Gillan, K. U. Ingold, J. Am. Chem. Soc. 1971, 93, 6551-6555
64. D. F. Bowman, T. Gillan, K. Ingold, J. Am. Chem. Soc. 1971, 93, 6555-6561.
65. The DFT calculations were performed using Turbomole 6.5. [
66. F. Furche, R. Ahlrichs, C. Hättig, W. Klopper, M. Sierka, F. Weigend, Comp. Mol. Sci. 2014, 4, 91-100 ] within Gaussian basis sets [
67. Gaussian 09 (RevisionB.01), M. J. Frisch et al., Gaussian, Inc., Wallingford CT, 2010]. Geometry optimizations were performed with the BP86 density functional and the triple-ζ basis set def2-TZVP, using the resolution of identity (RI-J) approximation. Single point energies were calculated with the double hybrid functional B2PLYP [
68. L. Goerigk, S. Grimme, Comp. Mol. Sci. 2014, 4, 576-600 ] and def2-TZVP as the basis set. Grimme's dispersion correction D3 was used in all calculations [
69. S. Grimme, Comp. Mol. Sci. 2011, 1, 211-228 ].