Asymmetric 1,3-dipolar cycloaddition reactions of benzonitrile oxide mediated by a chiral Lewis acid

European Journal of Organic Chemistry

Volumn , Issue 17, 2007, Pages 2859-2864

  Yamamoto, Hidetoshi ^a   Hayashi, Saori ^a   Kubo, Masashi ^a   Harada, Mayu ^a   Hasegawa, Masayuki ^a   Noguchi, Michihiko ^b   Sumimoto, Michinori ^a   Hori, Kenzi ^a  

^a YAMAGUCHI UNIVERSITY   (Japan)

^b YAMAGUCHI UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

Asymmetric synthesis; Chirality; Cycloaddition; Enantioselectivity; Heterocycles

Indexed keywords

EID: 34250897382     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601014     Document Type: Article

References (33)

1. For reviews, see: a) D. P. Curran (Ed.), Advances in Cycloaddition, JAI Press, Greenwich, 1988, vol. 1;
2. 1990, vol. 2;
3. 1993, vol. 3;
4. b) A. Padwa (Ed.), 1,3-Dipolar Cycloaddition Chemistry, Wiley, Toronto, 1984, vol. 1 and 2;
5. see also: c) J.-H. Chu, W.-S. Li, I. Chao, G.-H. Lee, W.-S. Chung, Tetrahedron 2006, 62, 7380-7389;
6. d) S. Gao, Z. Tu, C.-W. Kuo, J.-T. Liu, C.-M. Chu, C.-F. Yao, Org. Biomol. Chem. 2006, 4, 2851-2857;
7. e) J. B. F. N. Engberts, E. Fernandez, L. Garcia-Rio, J. R. Leis, J. Org. Chem. 2006, 71, 6118-6123;
8. f) K. Bala, H. C. Hailes, Synthesis 2005, 3423-3427.
9. a) H. Jiang, J. Zhao, X. Han, S. Zhu, Tetrahedron 2006, 62, 11008-11011;
10. b) U. Groselj, D. Bevk, R. Jakse, A. Meden, B. Stanovnik, J. Svete, Tetrahedron: Asymmetry 2006, 17, 1217-1237;
11. c) M. Benltifa, S. Vidal, D. Gueyrard, P. G. Goekjian, M. Msaddek, J.-P. Praly, Tetrahedron Lett. 2006, 47, 6143-6147;
12. d) S. P. Waters, M. W. Fennie, M. C. Kozlowski, Org. Lett. 2006, 8, 3243-3246.
13. In recent years, Lewis acid supported stereocontrol in nitrile oxide cycloaddition reactions has been developed independently, but the efficiency of the stereoselection was less satisfactory with the Lewis acid: a) G. Faita, A. Paio, P. Quadrelli, F. Rancati, P. Seneci, Tetrahedron 2001, 57, 8313-8322;
14. b) G. Faita, A. Paio, P. Quadrelli, F. Rancati, P. Seneci, Tetrahedron Lett. 2000, 41, 1265-1269;
15. c) P. Micúch, L. Fisera, M. K. Cyranski, T. M. Krygowski, J. Krajcik, Tetrahedron 2000, 56, 5465-5472;
16. d) P. Micúch, L. Fisera, M. K. Cyranski, T. M. Krygowski, Tetrahedron Lett. 1999, 40, 167-170.
17. [6]), Sibi et al. also reported a very enantioselective nitrile oxide cycloaddition reaction: M. P. Sibi, K. Itoh, C. P. Jasperse, J. Am. Chem. Soc. 2004, 126, 5366-5367.
18. a) H. Yamamoto, S. Watanabe, M. Hasegawa, M. Noguchi, S. Kanemasa, J. Chem. Res. (S) 2003, 284-286;
19. b) H. Yamamoto, S. Watanabe, K. Kadotani, M. Hasegawa, M. Noguchi, S. Kanemasa, Tetrahedron Lett. 2000, 41, 3131-3136.
20. Some of these results have been reported in a) Jpn. Kokai Tokkyo Koho, JP 2003-89697 (28th Mar. 2003) [Application No. JP 2001-283363 (18th Sep. 2001)];
21. b) Jpn. Kokai Tokkyo Koho, JP 2004-99470 (2nd Apr. 2004) [Application No. JP 2002-260653 (5th Sep. 2002)];
22. c) Jpn. Kokai Tokkyo Koho, JP 2005-8593 (13th Jan. 2005) [Application No. JP 2003-176878 (20th June, 2003)].
23. a) G. Desimoni, G. Faita, M. Guala, A. Laurenti, Eur. J. Org. Chem. 2004, 3057-3062;
24. b) S. Fukuzawa, K. Metoki, S. Esumi, Tetrahedron 2003, 59, 10445-10452;
25. c) G. Desimoni, G. Faita, M. Guala, C. Pratelli, J. Org. Chem. 2003, 68, 7862-7866;
26. d) D. A. Evans, J. Wu, J. Am. Chem. Soc. 2003, 125, 10162-10163;
27. e) G. Desimoni, G. Faita, M. Guala, C. Pratelli, Tetrahedron 2002, 58, 2929-2935;
28. f) S. Fukuzawa, H. Matsuzawa, K. Metoki, Synlett 2001, 709-711.
29. D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238-1256.
30. M. Christl, R. Huisgen, Chem. Ber. 1973, 106, 3345-3367.
31. W. Oppolzer, A. J. Kingma, S. K. Pillai, Tetrahedron Lett. 1991, 32, 4893-4896.
32. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03 (Revision C.02), Gaussian, Inc., Wallingford, CT, 2004.
33. T. Sakai, H. Mitsutomo, T. Korenaga, T. Ema, Tetrahedron: Asymmetry 2005, 16, 1535-1539.