Stereocontrolled 1,3-dipolar cycloadditions using Oppolzer's camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides
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Elsevier BV
Subject
Organic Chemistry,Drug Discovery,Biochemistry
Reference20 articles.
1. For an excellent recent review of asymmetric 1,3-dipolar cycloaddition reactions, see: Gothelf, K. V.; Jorgensen, K. A. Chem Rev.1998, 98, 863.
2. Some synthetic applications of azomethine ylides: (a) Confalone, P. N.; Huie, E. M. J. Am. Chem. Soc.1984, 106, 7175. (b) Kraus, G. A.; Nagy, J. O. Tetrahedron1985, 41, 3537. (c) DeShong, P.; Kell, D. A. Tetrahedron Lett.1986, 27, 3979. (d) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Am. Chem. Soc.1987, 109, 5523. (e) Takano, S.; Samizu, K.; Ogasawara, K. Chem. Lett.1990, 1239. (f) Sisko, J.; Weinreb, S. M. J. Org. Chem.1991, 56, 3210. (g) Garner, P.; Ho, W. B.; Shin, H. J. Am. Chem. Soc.1993, 115, 10742. (h) Henke, B. R.; Kouklis, A. J.; Heathcock, C. H. J. Org. Chem.1992, 57, 7056. (i) Denhart, D. J.; Griffith, D. A.; Heathcock, C. H. J. J. Org. Chem.1998, 63, 9616. (j) Osamu, I.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem.1999, 64, 587. (k) Coldham, I.; Crapnell, K. M.; Fernandez, J.-C.; Haxell, T. F. N.; Treacy, A. B.; Cole, S. J.; Hursthouse, M. B.; Moseley, J. D. Chem. Commun.1999, 1359.
3. (a) Padwa, A.; Chen, Y.-Y.; Chiacchio, U.; Dent, W. Tetrahedron1985, 41, 3529. (b) Deprez, P.; Royer, J.; Husson, H.-P. Tetrahedron: Asymmetry1991, 2, 1189. (c) Anslow, A. S.; Harwood, L. M.; Phillips, H.; Watkin, D.; Wong, L. F. Tetrahedron: Asymmetry1991, 2, 1343. (d) Allway, P.; Grigg, R. Tetrahedron Lett.1991, 32, 5817. (e) Williams, R. M.; Zhai, W.; Aldous, D. J.; Aldous, S. C. J. Org. Chem.1992, 57, 6527. (f) Negron, G.; Roussi, G.; Zhang, J. Heterocycles1992, 34, 293. (g) Takano, S.; Moriya, M.; Ogasawara, K. Tetrahedron: Asymmetry1992, 3, 681. (h) Allway, P.; Grigg, R. Tetrahedron Lett.1991, 32, 5817. (i) Peyronel, J. F.; Grisoni, S.; Carboni, B.; Courgeon, T.; Carrié, R. Tetrahedron1994, 50, 189. (j) Baldwin, J. E.; Turner, S. C. S.; Moloney, M. G. Synlett1994, 925. (k) Novello, F.; Prato, M.; Da Ros, T.; De Amici, M.; Bianco, A.; Toniolo, C.; Maggini, M. Chem. Commun.1996, 903. (l) Jones, R. C. F.; Howard, K. J.; Snaith, J. S. Tetrahedron Lett.1996, 37, 1707. (m) Fray, A. H.; Meyers, A. I. J. Org. Chem.1996, 61, 3362.
4. Preliminary communication: Garner, P., Dogan, O. J. Org. Chem.1994, 59, 4.
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