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N-Hydroxy amino acids have been found as components of depsipeptide antibiotics: M. Lorca, and M. Kurosu Tetrahedron Lett. 2001 2431 2434
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Kurosu, M.2
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Another N-hydroxy compound, which displays useful pharmacological properties is the 5-lipoxygenase inhibitor Zileuton (D.W. Brooks, R.L. Bell, G.W. Carter, L.M. Dube, and P.D. Rubin Drugs Future 18 1993 616 618)
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Rubin, P.D.5
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20
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J.A. Marco, M. Carda, J. Murga, S. Rodríguez, E. Falomir, and M. Oliva Tetrahedron: Asymmetry 9 1998 1679 1701
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21
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0032557720
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M. Carda, J. Murga, S. Rodríguez, F. González, E. Castillo, and J.A. Marco Tetrahedron: Asymmetry 9 1998 1703 1712
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33748899259
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J.A. Marco, M. Carda, F. González, S. Rodríguez, and J. Murga Liebigs Ann. Chem. 1996 1801 1810
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M. Carda, S. Rodríguez, J. Murga, E. Falomir, J.A. Marco, and H. Röper Synth. Commun. 29 1999 2601 2610
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27
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J.A. Marco, M. Carda, J. Murga, R. Portolés, E. Falomir, and J. Lex Tetrahedron Lett. 1998 3237 3240
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0034693123
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1,3-Dipolar cycloadditions of this nitrone have also been investigated: M. Carda, R. Portolés, J. Murga, S. Uriel, J.A. Marco, L.R. Domingo, R.J. Zaragozá, and H. Roeper J. Org. Chem. 65 2000 7000 7009
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Roeper, H.8
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29
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19344376705
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note
-
9 which was unreactive towards organometallics
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30
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0036245778
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2OTPS group. For a preliminary account of the results described here, see: R. Portolés, J. Murga, E. Falomir, M. Carda, S. Uriel, and J.A. Marco Synlett 2002 711 714
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Murga, J.2
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Carda, M.4
Uriel, S.5
Marco, J.A.6
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31
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19344373261
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note
-
We have studied the formation of the nitrone with the aid of quantum-mechanical ab initio methods. The non-isolated E nitrone was found to be more stable than the Z-isomer by over 3 kcal/mol. This indicates that the formation of the Z-nitrone is subject to kinetic control. Preliminary results of studies on possible transition states suggest that that leading to the isolated Z-nitrone is lower in energy than the alternative transition state leading to the E-isomer (unpublished results with S. Safont)
-
-
-
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32
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19344368164
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note
-
An exception was oxazolidinone 6f, where unequivocal NOE measurements were not possible due to overlapping of the key signals. In this case, however, the configuration was unequivocally determined by means of X-ray diffraction analysis of product 7f
-
-
-
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33
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19344364634
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note
-
Crystallographic data of 4b, 4e and 7f have been deposited at the Cambridge Crystallographic Data Centre (deposition numbers from CCDC-177985 to CCDC-177987)
-
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35
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85033642706
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A. Dondoni, S. Franco, S.L. Merchán, P. Merino, and T. Tejero Synlett 1993 78 80
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A. Dondoni, F. Junquera, F.L. Merchán, P. Merino, and T. Tejero Synthesis 1994 1450 1456
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D.D. Dhavale, V.N. Desai, M.D. Sindkhedkar, R.S. Mali, C. Castellari, and C. Trombini Tetrahedron: Asymmetry 8 1997 1475 1486
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For an ab initio study of the reaction of Grignard reagents with chiral nitrones, see: P. Merino, and T. Tejero Tetrahedron 57 2001 8125 8128
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M. Carda, E. Castillo, S. Rodríguez, F. González, and J.A. Marco Tetrahedron: Asymmetry 12 2001 1417 1429
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