Abstract
2-Trifluoromethyl-substituted 1,2,3,6-tetrahydro-2-pyridyl carboxylates were synthesized in one step by the aza Diels—Alder reactions of methyl trifluoropyruvate sulfonyl- and phosphorylimines with 1,3-dienes.
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V. Hruby, F. Al-Obeidi, and W. Klazmierski, Biochem. J., 1990, 268, 249.
J. T. Welch, Tetrahedron, 1987, 43, 3123; b) J. T. Welch, in Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symposium Series 456 T. J. Welch Ed., 1991, 1; c) K. Burger, K. Muetze, W. Hollweck, and B. Koksch, Tetrahedron, 1998, 54, 5915.
S. N. Osipov, C. Bruneau, M. Picquet, A. F. Kolomiets, and P. H. Dixneuf, Chem. Commun., 1998, 2053; b) S. N. Osipov, N. M. Kobel´kova, G. T. Shchetnikov, A. F. Kolomiets, C. Bruneau, and P. H. Dixneuf, Synlett, 2001, 621; c) S. N. Osipov, O. I. Artyushin, A. F. Kolomiets, C. Bruneau, M. Picquet, and P. H. Dixneuf, Eur. J. Org. Chem., 2001, 20, 3891.
A. Mazon and C. Najera, Tetrahedron: Asymmetry, 1997, 8, 1855.
A. Whilting and C. M. Windsor, Tetrahedron, 1998, 54, 6035.
S. N. Osipov, N. D. Chkanikov, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 1384 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 35, 1256 (Engl. Transl.)]; b) S. N. Osipov, N. D. Chkanikov, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 1648 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 38, 1512 (Engl. Transl.)].
S. N. Osipov, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 132 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 37, 122 (Engl. Transl.)].
S. N. Osipov, N. M. Kobel´kova, A. F. Kolomiets, K. Burger, K. Pumper, and B. Koksch, Synlett, 2001, 1287; b) N. M. Kobel´kova, S. N. Osipov, and A. F. Kolomiets, Izv. Akad. Nauk, Ser. Khim., 2001, 997 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1041].
H. Waldman, Synthesis, 1994, 535; b) D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, 1987.
J. W. Reed, M. B. Purvis, D. G. I. Kingston, A. Biot, and F. Gossole, J. Org. Chem., 1989, 54, 1161; b) F. Machetti, F. M. Cordero, F. De Sarlo, A. Guarna, and A. Brand, Tetrahedron Lett., 1996, 37, 4205.
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Kobel"kova, N.M., Osipov, S.N. & Kolomiets, A.F. Aza Diels—Alder reactions of methyl trifluoropyruvate sulfonyl- and phosphorylimines with 1,3-dienes. Russian Chemical Bulletin 51, 1298–1302 (2002). https://doi.org/10.1023/A:1020964916405
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DOI: https://doi.org/10.1023/A:1020964916405