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0018777888
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To the best of our knowledge, our procedure is the first direct diastereoselective vinylation at a lactam carbonyl group. The reported cyanide addition to a lactam carbonyl group and the subsequent substitution by a vinyl group was not adopted, because partial epimerization during the cyanide addition was consistently observed: R. D. Gless, H. Rapoport, J. Org. Chem. 1979, 44, 1324; M. Rubiralta, E. Giralt, A. Diez, Piperidine, Elsevier, New York, 1991, pp 235-244;
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Gless, R.D.1
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17
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0012810872
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Elsevier, New York
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To the best of our knowledge, our procedure is the first direct diastereoselective vinylation at a lactam carbonyl group. The reported cyanide addition to a lactam carbonyl group and the subsequent substitution by a vinyl group was not adopted, because partial epimerization during the cyanide addition was consistently observed: R. D. Gless, H. Rapoport, J. Org. Chem. 1979, 44, 1324; M. Rubiralta, E. Giralt, A. Diez, Piperidine, Elsevier, New York, 1991, pp 235-244;
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For related examples, see M. J. Fisher, L. E. Overman, J. Org. Chem. 1990, 55, 1447; T. Hosaka, Y. Torisawa, M. Nakagawa, Tetrahedron Lett. 1997, 38, 3535.
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For related examples, see M. J. Fisher, L. E. Overman, J. Org. Chem. 1990, 55, 1447; T. Hosaka, Y. Torisawa, M. Nakagawa, Tetrahedron Lett. 1997, 38, 3535.
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84981409984
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L. Kisfaludy, M. Löw, O. Nyeki, T. Szirtes, I. Schön, Justus Liebigs Ann. Chem. 1973, 1421. This process was superior to other lactamizations in terms of both yield and convenience.
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29
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84920354303
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note
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[1c] We thank Professor Takenori Kusumi of Tokushima University and Professor Hiroshi Kakisawa of the University of Tsukuba for kindly providing spectral data of the fluvirucins.
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