Diastereoselective iodoamidation of 3-acetyloxybut-1-enylamines: simple synthesis of a precursor of aza sugars involving a pyrrolidine ring
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Woo Song Lee, Ki Chang Jang, Jin Hyo Kim and Ki Hun Park
Abstract
3-Acetyloxybut-1-enylamines 3–9 were easily transformed using iodine to pyrrolidine derivatives 3a–9a, precursors for aza sugars, via a diastereoselective iodoamidation.
References
S. Horri, H. Fukase, T. Matsuo, Y. Kameda, N. Asano and K. Matsui, J. Med. Chem., 1986, 29, 1038 CrossRefCAS.
M. A. Spearman, J. C. Jamieson and J. A. Wright, Exp. Cell Res., 1987, 168, 116 CAS; K. Tsukamoto, A. Uno, S. Shimada and G. Imokaw, Clin. Res., 1989, 37A, 722 Search PubMed.
A. Karpas, G. W. J. Fleet, R. A. Dwek, S. Petursson, S. K. Mamgoong, N. G. Ramsden, G. S. Jacob and T. W. Rademacher, Proc. Natl. Acad. Sci. U.S.A., 1988, 85, 9229 CAS; G. W. J. Fleet, FEBS Lett., 1988, 237, 128 CrossRefCAS.
G. Kinast and M. Schedel, Angew. Chem. Int. Ed. Engl., 1981, 20, 805 CrossRef; A. Vasella and R. Voeffray, Helv. Chim. Acta, 1982, 65, 1134 CrossRefCAS; H. Iida, N. Yamazaki and C. Kibayashi, J. Org. Chem., 1987, 52, 3337 CrossRefCAS; D. Beaupere, B. Stasik, R. Uzan and G. Demailly, Carbohydr. Res., 1989, 191, 163 CrossRefCAS; C. H. von der Osten, A. J. Sinskey, C. F. Barbas, R. L. Pederson, Y.-F. Wang and C.-H. Wong, J. Am. Chem. Soc., 1989, 111, 3924 CrossRefCAS; G. W. J. Fleet, N. M. Carpenter, S. Petursson and N. J. Ramsden, Tetrahedron Lett., 1990, 31, 409 CrossRefCAS; A. Straub, F. Effenberger and P. Fischer, J. Org. Chem., 1990, 55, 3926 CrossRefCAS.
D. P. Schumacher and S. S. Hall, J. Am. Chem. Soc., 1982, 104, 6076 CrossRefCAS; H. H. Baer and M. Zamkanei, J. Org. Chem., 1988, 53, 4786 CrossRefCAS; R. Ballini, E. Marcantoni and M. Petrini, J. Org. Chem., 1992, 57, 1316 CrossRefCAS.
G. W. J. Fleet, S. J. Nicolas, P. W. Smith, S. V. Evans, L. E. Fellows and R. J. Nash, Tetrahedron Lett., 1985, 26, 3127 CrossRefCAS; N. Asano, K. Oseki and K. Matsui, J. Med. Chem., 1994, 37, 3710.
H. Setoi, H. Takeno and M. Hashimoto, J. Org. Chem., 1985, 50, 3948 CrossRefCAS; R. B. B. III, J.-R. Choi, W. D. Montgomery and J. K. Cha, J. Am. Chem. Soc., 1989, 111, 2580 CrossRef.
S. Nukui, M. Sodeoka, H. Sasaki and Shibasaki, J. Org. Chem., 1995, 60, 398 CrossRefCAS.
F. J. Sardina and H. Rapoport, Chem. Rev., 1996, 96, 1825 CrossRefCAS.
W. D. Lubell and H. Rapoport, J. Am. Chem. Soc., 1987, 109, 236 CrossRefCAS.
M. Gerspacher and H. Rapoport, J. Org. Chem., 1991, 56, 3700 CrossRefCAS.
S. Robin and G. Rousseau, Tetrahedron, 1998, 54, 13681 CrossRefCAS.
H. Takahata, T. Tamotsu and Y. Takao, J. Org. Chem., 1989, 54, 4812 CrossRefCAS; H. Takahata, K. Yamazaki, T. Takamatsu, T. Yamazaki and T. Momose, J. Org. Chem., 1990, 55, 3947 CrossRefCAS.
Y. Tamaru, S. Kawamura, K. Tanaka and Z. Yoshida, Tetrahedron Lett., 1984, 25, 1063 CrossRefCAS; Y. Tamaru, S.-i. Kawamura, T. Bando, K. Tanaka, M. Hojo and Z.-i. Yoshida, J. Org. Chem., 1988, 53, 5491 CrossRef.
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