Proline as Lewis base catalyst: Diastereoselective synthesis of isoxazoline-N-oxide through [3 + 2] cycloaddition

Organic Letters

Volumn 10, Issue 18, 2008, Pages 4113-4116

  Duan, Haifeng ^a   Sun, Xiaohua ^a   Liao, Wenyan ^a   Petersen, Jeffrey L ^a   Shi, Xiaodong ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE OXIDE; ESTER; ISOXAZOLE DERIVATIVE; PROLINE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; ENZYME SPECIFICITY; STEREOISOMERISM;

CATALYSIS; CYCLIC N-OXIDES; CYCLIZATION; ESTERS; ISOXAZOLES; PROLINE; STEREOISOMERISM; SUBSTRATE SPECIFICITY; VINYL COMPOUNDS;

EID: 55949133792     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801656y     Document Type: Article

References (44)

1. (a) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; Wiley-VCH: Weinheim, Germany, 2004.
2. (b) Enantioselective Organocatalysis; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, Germany, 2007.
3. For reviews, see: (c) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719-724.
4. (d) Marigo, M.; Jorgensen, K. A. Chem. Commun. 2006, 2001-2011.
5. (e) Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P.; Rutjes, F. Chem. Soc. Rev. 2008, 37, 29-41.
6. Selected reports: (a) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000. 122, 2395-2596.
7. (b) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244.
8. (c) Cordova, A.; Notz, W.; Zhong, G. F.; Betancort, J. M.; Barbas, C. F. J. Am. Chem. Soc. 2002, 124, 1842-1843.
9. (d) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212-4215.
10. (e) Wang, J.; Xie, H. X.; Li, H.; Zu, L. S.; Wang, W. Angew. Chem., Int. Ed. 2008, 47, 4177-4179.
11. Selected reports: (a) List, B J. Am. Chem. Soc. 2002, 124, 5656-5657.
12. (b) Zhong, G. F. Angew. Chem., Int. Ed. 2003, 42, 4247-4250.
13. (c) Merino, P.; Tejero, T. Angew. Chem., Int. Ed. 2004, 43, 2995-2997.
14. (d) Franzen, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Kjaersgaard, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296-18304.
15. Selcted reports: (a) Ouellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C J. Am. Chem. Soc. 2005, 127, 32-33.
16. (b) Marigo, M.; Franzen, J.; Poulsen, T. B.; Zhuang, W.; Jorgensen, K. A. J. Am. Chem. Soc. 2005, 127, 6964-6965.
17. (c) Yang, J. W.; Fonseca, M. T. H.; List, B. J. Am. Chem. Soc. 2005, 127, 15036-15037.
18. France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985-3012.
19. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560-1638.
20. Sun, X.; Sengupta, S.; Petersen, J. L.; Wang, H.; Lewis, J. P.; Shi, X.-D. Org. Lett. 2007, 9, 4495-4498.
21. (a) Torssell, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH: New York, 1988.
22. (b) Ono, N. The Nitro Group in Organic Synthesis; John Wiley & Sons-VCH: New York, 2001; pp 249-301.
23. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137-165.
24. Selected examples of nitro compound [3 + 2] reactions: (a) Denmark, S. E.; Seierstad, M.; Herbert, B. J. Org. Chem. 1999, 64, 884-901.
25. (b) Voituriez, A.; Moulinas, J.; Kouklovsky, C.; Langlois, Y. Synthesis 2003, 9, 1419-1426.
26. (c) Roger, P. Y.; Durand, A. C.; Rodriguez, J.; Dulcere, J. P. Org. Lett. 2004, 6, 2027-2029.
27. (d) Arrieta, A.; Otaegui, D.; Zubia, A.; Cossio, F. P.; Diaz-Ortiz, A.; de la Hoz, A.; Herrero, M. A.; Prieto, P.; Foces-Foces, C.; Pizarro, J. L.; Arriortua, M. I. J. Org. Chem. 2007, 72. 4313-4322.
28. (a) Groutas, W. C.; Venkataraman, R.; Chong, L. S.; Yoder, J. E.; Epp, J. B.; Stanga, M. A.; Kim, E.-H. Bioorg. Med. Chem. 1995, 3, 125-128.
29. (b) Mousa, S. A.; Olson, R. E.; Bozarth, J. M.; Friedman, P. A. J. Cardiovasc. Pharmacol. 1998, 32, 169-176.
30. (a) Rosini, G.; Galarini, R. V.; Marotta, E.; Righi, P. J. Org. Chem. 1990, 55, 781-783.
31. (b) Galli, C.; Marotta, E.; Righi, P.; Rosini, G. J. Org. Chem. 1995, 60, 6624-6626.
32. (c) Arai, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 2525-2534.
33. (d) Marotta, E.; Baravelli, M.; Maini, L.; Righi, P.; Rosini, G. J. Org. Chem. 1998, 63, 8235-8246.
34. (e) Gil, M. V.; Roman, E.; Serrano, J. A. Tetrahedron Lett. 2000, 41, 3221-3224.
35. (f) Scardovi, N.; Casalini, A.; Peri, F.; Righi, P. Org. Lett. 2002, 4, 965-968.
36. (a) Whitney, R. A.; Nicholas, E. S. Tetrahedron Lett. 1981, 22, 3371-3374.
37. (b) Torssell, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; Feuer, H., Ed.; VCH: Weinheim, 1988; pp 55-74.
38. (c) Kunetsky, R. A.; Dilman, A. D.; Ioffe, S. L.; Struchkova, M. I.; Strelenko, Y. A.; Tartakovsky, V. A. Org. Lett. 2003, 5, 4907-4909.
39. (d) Kunetsky, R. A.; Dilman, A. D.; Struchkova, M. I.; Belyakov, P. A.; Tartakovsky, V. A.; Ioffe, S. L. Synthesis 2006, 13, 2265-2270.
40. See Supporting Information.
41. Machetti, F.; Cecchi, L.; Trogu, E.; De Sarlo, F. Eur. J. Org. Chem. 2007, 4352-4359.
42. (a) Marotta, E.; Micheloni, L. M.; Scardovi, N.; Righi, P. Org. Lett. 2001, 3, 727-729.
43. (b) Fuller, A. A.; Chen, B.; Minter, A. R.; Mapp. A. K. J. Am. Chem. Soc. 2005, 127, 5376-5383.
44. (c) Gil, M. V.; Roman, E.; Serrano, J. A. Tetrahedron 2007, 58, 2167-2173.