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Reactions of racemic benzyl tert-butyl sulfoxide with several N-phenylimines are highly stereoselective (see ref 6e). A similar behavior was observed in the synthesis of aziridines from racemic α-halosulfoxides and imines (Satoh, T.; Oohara, T.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 4093). Racemic fluoromethyl phenyl sulfoxide reacts with N-phenyl arylimines with moderate to very high selectivity, depending on the nature of the aryl group (Mahidol, C.; Reutrakul, V.; Prapansiri, V.; Panyanchotipun, C. Chem. Lett. 1984, 969).
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34
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0002763805
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Reactions of racemic benzyl tert-butyl sulfoxide with several N-phenylimines are highly stereoselective (see ref 6e). A similar behavior was observed in the synthesis of aziridines from racemic α-halosulfoxides and imines (Satoh, T.; Oohara, T.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 4093). Racemic fluoromethyl phenyl sulfoxide reacts with N-phenyl arylimines with moderate to very high selectivity, depending on the nature of the aryl group (Mahidol, C.; Reutrakul, V.; Prapansiri, V.; Panyanchotipun, C. Chem. Lett. 1984, 969).
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Mahidol, C.1
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0000804599
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García Ruano, J. L.; Fernández, I.; del Prado Catalina, M.; Hermoso, J. A.; Sanz-Aparicio, J.; Martínez-Ripoll, M. J. Org. Chem. 1998, 63, 7157.
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Martínez-Ripoll, M.6
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36
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0343896747
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3. Nevertheless, we must take into account that these reactions must be strongly exothermic. Thus, according to the Hammond postulate, one must expect a reactant-like transition state, involving a greater distance for the incipient new C-C bond and thus resulting in a weaker repulsive interaction (Ph/Tol) because of the long distance between the two groups
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3. Nevertheless, we must take into account that these reactions must be strongly exothermic. Thus, according to the Hammond postulate, one must expect a reactant-like transition state, involving a greater distance for the incipient new C-C bond and thus resulting in a weaker repulsive interaction (Ph/Tol) because of the long distance between the two groups.
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37
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0342591087
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5 and which evidenced a strong decrease in the stereoselectivity of reactions of achiral imines with alkyl p-tolyl sulfoxides
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5 and which evidenced a strong decrease in the stereoselectivity of reactions of achiral imines with alkyl p-tolyl sulfoxides.
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40
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0002661099
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Brunet, E.; Gallego, M. T.; García Ruano, J. L.; Alcudia, F. Tetrahedron 1986, 42, 1423.
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Alcudia, F.4
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41
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84986799903
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2 (Alcudia, F.; Brunet, E.; Carreño, M. C.; Gallego, M.; García Ruano, J. L. J. Chem. Soc., Perkin Trans. 2 1983, 937) showed that the interactions controlling the conformational behavior were similar in both series.
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Alcudia, F.1
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Hoyos, M.A.4
Prados, P.5
Rodríguez, J.H.6
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42
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0343025320
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2 (Alcudia, F.; Brunet, E.; Carreño, M. C.; Gallego, M.; García Ruano, J. L. J. Chem. Soc., Perkin Trans. 2 1983, 937) showed that the interactions controlling the conformational behavior were similar in both series.
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J. Chem. Soc., Perkin Trans. 2
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Alcudia, F.1
Brunet, E.2
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43
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0343106042
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Carretero, J. C.; García Ruano, J. L.; Martínez, M. C.; Rodriguez, J. H. Tetrahedron 1985, 41, 2419.
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Rodriguez, J.H.4
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44
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0343896742
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A detailed discusion of the conformational behavior of these substrates appears in ref 25
-
) A detailed discusion of the conformational behavior of these substrates appears in ref 25.
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