1,3-Dipolar cycloaddition of azomethine ylides to alkenylboronates: Synthesis of boronic ester substituted pyrrolidine derivatives and asymmetric approaches

Bulletin of the Korean Chemical Society

Volumn 26, Issue 5, 2005, Pages 717-718

  Zong, Kyukwan ^a  

^a Chonbuk National University   (South Korea)

Author keywords

1,3 Dipolar cycloaddition; Alkenylboronic esters; Azomethine ylide

Indexed keywords

EID: 20444482499     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2005.26.5.717     Document Type: Article

References (18)

1. For reviews of 1,3-dipolar cycloadditions, see: (a) Carruthers, W. Cycloadditions in Organic Synthesis; Pergamon Press: Exter, Great Britain, 1990; Vol. 8, Chap. 6.
2. (b) Huisgen, R. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vol. 1, Chap. 1.
3. (c) Curran, D. P. Advances in Cycloadditions; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1988; Vol. 1, p280.
4. For azomethine ylide cycloadditions, see: (a) Terao, Y.; Kotaki, H.; Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1985, 33, 2762.
5. (b) Padwa, A.; Chen, Y.-Y.; Chiachio, U.; Dent, W. Tetrahedron 1985, 41, 3529.
6. (c) Meyers, A. I.; Fray, A. H. Tetrahedron Lett. 1992, 33, 3575.
7. For the synthesis of 3-pyrrolidine derivatives, see: (a) Krether, R.; Pawalczyk, H. Tetrahedron Lett. 1966, 2591.
8. (b) Lukes, R.; Pergal, M. Coll. Czech. Chem. Comm. 1962, 27, 1387.
9. (c) Jaeger, E.; Biel, J. H. J. Org. Chem. 1965, 30, 740.
10. (d) Belfaitah, A.; Isly, M.; Carboni, B. Tetrahedron Lett. 2004, 45, 1969.
11. (e) Bowers Nemia, M. M.; Lee, J.; Joulli, M. M. Synth. Commun. 1983, 13, 1117.
12. (f) Brown, H. C.; Vara Prasad, J. V. N.; Gupta, A. K. J. Org. Chem. 1986, 51, 4296.
13. Rasset-Deloge, C.; Martinez-Fresneda, P.; Vaultier, M. Bull. Soc. Chim. Fr. 1992, 129, 285.
14. For asymmetric 1,3-dipolar cycloadditions, see: (a) Kanemasa, S.; Kobayashi, S.; Nishiuchi, M.; Yamamoto, H.; Wada, E. Tetrahedron Lett. 1991, 32, 6367.
15. (b) Curran, D. P.; Jeong, K.-S.; Heffner, T. A. J. Am. Chem. Soc. 1989, 111, 9238.
16. (c) Kawanami, T.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1987, 60, 4190.
17. Wallace, R. H.; Zong, K. J. Organomet. Chem. 1999, 551(2), 87.
18. Matteson, D. S. J. Am. Chem. Soc. 1962, 27, 3712.