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P. R. Bonneau, F. Hasani, C. Plouffe, E. Malefant, S. R. La-Plante, I. Guse, W. W. Ogilvie, R. Plante, W. C. Davinson, J. L. Hopkins, M. M. Morelock, M. G. Cordingley, R. Déziel, J. Am. Chem. Soc. 1999, 121, 2965.
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[12a] B. M. McKittrick, K. Ma, K. Huie, N. Yumibe, H. Davis Jr., J. W. Clader, M. Czarniecki, J. Med. Chem. 1998, 41, 752.
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[12b] G. Wu, Y. Wong, X. Chen, Z. Ding, J. Org. Chem. 1999, 64, 3714.
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0001700588
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Benzodiazepine derivatives 1 were prepared according to a procedure described in the literature: [14a] L. H. Sternbach, E. Reeder, J. Org. Chem. 1961, 26, 4936.
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22
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0025677291
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Just a few examples of Staudinger reactions involving ketimines have been previously described, apart from the reaction described in ref. [13]. [15a] J. W. Skiles, D. McNeil, Tetrahedron Lett. 1990, 31, 7277.
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Skiles, J.W.1
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24
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8244235132
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[15c] C. Palomo, J. M. Aizpurua, J. M. García, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, J. Server-Carrió, A. Linden, J. Org. Chem. 1997, 62, 2070.
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Palomo, C.1
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25
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0037009717
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[15d] The Staudinger reaction of ketimines derived from 7-oxanorbornenone has been reported recently: O. Arjona, A. G. Csákÿ, M. C. Murcia, J. Plumet, Tetrahedron Lett. 2002, 43, 6405.
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Arjona, O.1
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26
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1242316833
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note
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The other methylene proton at δ = 3.83 (d, J = 13.6 Hz) only correlates with the carbonyl carbon atoms.
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27
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1242316834
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note
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At the magnetic field used (7 T) the chemical shift difference between the amide carbon atoms was too small (Δδ = 0.024 ppm, 1.8 Hz) to allow for their unequivocal assignment.
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28
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1242339465
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note
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The correlation of this carbon with the proton of the chlorobenzene ring appearing at δ = 7.16 ppm (d, J = 13.6 Hz) allows its assignment.
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29
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0037073894
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For studies on the mechanism of the Staudinger reaction, see: [19a] A. Venturini, J. González, J. Org. Chem. 2002, 67, 9089.
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J. Org. Chem.
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Venturini, A.1
González, J.2
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30
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1242294286
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and references cited therein
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[19b] J. A. Sordo, J. González, T. L. Sordo, J. Am. Chem. Soc. 1992, 114, 6248, and references cited therein.
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Sordo, J.A.1
González, J.2
Sordo, T.L.3
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31
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0032707721
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For a recent review of the asymmetric Staudinger reactions including mechanistic considerations, see: C. Palomo, J. M. Aizpurua, I. Ganboa, M. Oiarbide, Eur. J. Org. Chem. 1999, 3223.
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Eur. J. Org. Chem.
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Palomo, C.1
Aizpurua, J.M.2
Ganboa, I.3
Oiarbide, M.4
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32
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0033525683
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A similar stereochemical result has been reported in the Staudinger reaction of cyclic aldimines: B. Alcaide, A. Rodríguez-Vicente, Tetrahedron. Lett. 1999, 40, 2005-2006.
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Tetrahedron. Lett.
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Alcaide, B.1
Rodríguez-Vicente, A.2
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33
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33751385142
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For calculations relative to the torquoelectronic effect on the ketene-imine cycloaddition, see: R. López, T. L. Sordo, J. A. Sordo, J. González, J. Org. Chem. 1993, 58, 7036.
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J. Org. Chem.
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López, R.1
Sordo, T.L.2
Sordo, J.A.3
González, J.4
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36
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0030870477
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[23c] C. Palomo, J. M. Aizpurua, M. Legido, A. Mielgo, R. Galarza, Chem. Eur. J. 1997, 3, 1432.
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Palomo, C.1
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Legido, M.3
Mielgo, A.4
Galarza, R.5
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37
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1242271884
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note
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1H NMR spectrum of compound 2 h measured at room temperature showed broad signals for the aromatic protons, which resolved into well-defined multiplets when the spectrum was acquired at 233 K. At this temperature all signals of the phenyl substituent become inequivalent. This observations are consistent with restricted rotation of the phenyl group, most probably due to steric interactions.
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38
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0001521888
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For recent reviews of the formation of asymmetric quaternary carbon centers see: [25a] K. Fuji, Chem. Rev. 1993, 93, 2037.
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(1993)
Chem. Rev.
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Fuji, K.1
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40
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1242316837
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note
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[25c] Palomo and co-workers (see ref. [15c]) have reported the application of [2+2] cycloaddition reactions to the construction of quaternary stereocenters.
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41
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0036008108
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[26a] E. Alonso, C. del Pozo, J. González, J. Chem. Soc., Perkin Trans. 1 2002, 571.
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(2002)
J. Chem. Soc., Perkin Trans. 1
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Alonso, E.1
Del Pozo, C.2
González, J.3
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42
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0035929452
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[26b] E. Alonso, F. López-Ortiz, C. del Pozo, E. Peralta, A. Macías, J. González, J. Org. Chem. 2001, 66, 6333.
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J. Org. Chem.
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Alonso, E.1
López-Ortiz, F.2
Del Pozo, C.3
Peralta, E.4
Macías, A.5
González, J.6
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43
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1242271883
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note
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13C, DEPT, and 2D HMQC, HMBC and NOESY NMR spectra.
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44
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1242294285
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note
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The diastereotopic methylene protons of the benzyloxy groups showed three correlations in the HMBC spectrum: with the quaternary carbons corresponding to the carbamate and the ipso carbon, and with the ortho carbons of the phenyl ring. The protons linked to these carbons were assigned from their correlations observed in the HMQC spectrum: for the pair of protons at δ = 4.19 ppm and 4.81 ppm (J = 12.2 Hz), the ortho protons of the phenyl ring appear at δ = 7.23 ppm, while for those at δ = 4.67 and 4.84 ppm (J = 12.6 Hz) the corresponding ortho protons were identified as a multiplet at δ = 7.03 ppm.
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45
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1242339469
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note
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The N-nitroso derivative 4 was prepared as described in ref.[4b].
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47
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85022475304
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G. I. Georg (Ed.), VCH Publishers, Inc., New York
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See, for example, The Organic Chemistry of β-Lactams, G. I. Georg (Ed.), VCH Publishers, Inc., New York, 1993, p. 303-306.
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(1993)
The Organic Chemistry of β-Lactams
, pp. 303-306
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49
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1242294287
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SADABS: G. M. Sheldrick, University of Göttingen, Germany, 1996. Program for absorption corrections using Bruker CCD data
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SADABS: G. M. Sheldrick, University of Göttingen, Germany, 1996. Program for absorption corrections using Bruker CCD data.
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50
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1242271882
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BRUKER SHELXTL-PC: G. M. Sheldrick, University of Göttingen, Germany, 1997
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BRUKER SHELXTL-PC: G. M. Sheldrick, University of Göttingen, Germany, 1997.
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