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85128559023
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2 was used for other ArCl substrates.
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19
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0033602522
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G.A.M. Giardina, L.F. Raveglia, M. Grugni, H.M. Sarau, C. Farina, A.D. Medhurst, D. Graziani, D.B. Schmidt, R. Rigolio, M. Luttmann, S. Cavagnera, J.J. Foley, V. Vecchietti, D. W. P. Hay, J. Med. Chem. 1999, 42, 1053-1065.
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0001261774
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A similar mechanism has been proposed for the formation of 2-oxazolidone from β-iodourethane, see; C. Heathcock, A. Hassner, Angew. Chem. 1963, 75, 344.
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33749819616
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note
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The yields are lower with benzoate protected substrate 35a due to competing hydrolysis of the starting amine. With silyl protection the % yields were in the 80s.
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32
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0029874188
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a) J.P. Wolfe, R.A. Rennels, S.L. Buchwald, Tetrahedron 1996, 21, 7525-7546;
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d) for intramolecular amidation, see: J.P. Wolfe, R.A. Rennels, S.L. Buchwald, Tetrahedron 1996, 52, 7525-7546.
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15144354135
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For some related work in this area, see: b) J.A. Tucker, D.A. Allwine, K.C. Grega, M.R. Barbachyn, J.L. Klock, J.L. Adamski, S.J. Brickener, D.K. Hutchinson, C.W. Ford, G.E. Zurenko, R.A. Conradi, P.S. Burton, R.M. Jensen, J. Med. Chem. 1998, 41, 3727-3735;
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c) M.J. Genin, D.K. Hutchinson, D.A. Allwine, J.B. Hester, D.E. Hemmert, S.A. Garmon, C.W. Ford, G.E. Zurenko, J.C. Hamel, R.D. Schaadt, D. Stapert, B.H. Yagi, J.M. Friis, E.M. Shobe, W.J. Adams, J. Med. Chem. 1998, 41, 5144-5147;
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d) D.M. Gleave, S.J. Brickner, P.R. Manninen, D.A. Allwine, K.D. Lovasz, D.C. Rohrer, J.A. Tucker, G.E. Zurenko, C.W. Ford, Bioorg. Med. Chem. Lett. 1998, 8, 1231-1236;
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0034794463
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Improvements including use of catalytic copper salt as well as significantly milder conditions have been described: a) A. Klapars, J.C. Antilla, X. Huang, S.L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727-7729.
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