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Blaser, H.-U.1
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Reviews:
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Melchiorre P., Marigo M., Carlone A., and Bartoli G. Angew. Chem., Int. Ed. 47 (2008) 6138
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Reviews:
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Malkov A.V., Stončius S., MacDougall K.N., Mariani A., McGeoch G.D., and Kočovský P. Tetrahedron 62 (2006) 264
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While we were proceeding with the European Patent application (see Ref. 14) and completing the experiments for submitting the present manuscript a communication was published:
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While we were proceeding with the European Patent application (see Ref. 14) and completing the experiments for submitting the present manuscript a communication was published:. Zheng H., Deng J., Lin W., and Zhang X. Tetrahedron Lett. 48 (2007) 7934
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35
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67649594699
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note
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For catalyst 1 several experiments of reduction reactions run at low temperature did not show any improvement in the stereoselection of the process.
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36
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33845943843
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For a discussion on the relative basicity of pyridine ring as function of the substituents see: The fact that 4 chloro picolinamide 29 behaved better than 4-methyl picolinamide 27 seems to suggest that electronic factors play a major role in fine tuning the catalytic activity and determining an optimum arrangement of the catalyst-trichlorosilane-imine adduct.
-
For a discussion on the relative basicity of pyridine ring as function of the substituents see: The fact that 4 chloro picolinamide 29 behaved better than 4-methyl picolinamide 27 seems to suggest that electronic factors play a major role in fine tuning the catalytic activity and determining an optimum arrangement of the catalyst-trichlorosilane-imine adduct. Brotzel F., Kempf B., Singer T., Zipse H., and Mayr H. Chem.-Eur. J. 13 (2007) 336
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37
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67649606647
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note
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Further details about the enantioselective reduction of aryl-alkyl ketones will be reported (manuscript in preparation).
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-
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38
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67649579648
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note
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Since in his report (Ref. 15) Zhang normally used catalyst 1 in 20 mol % amount, for sake of comparison we preferred to report in Table 5 the results obtained by us by employing both catalysts 1 and with 29 at 10%. In our hands catalyst 1 performed often better at 0 °C than at lower temperature.
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39
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67649579647
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European Patent Application. n.EP07023240.0, September 22, 2008
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Guizzetti, S.; Benaglia, M. European Patent Application. n.EP07023240.0, September 22, 2008.
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67649609399
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Enantioselective reductive amination: selected references for organometallic systems
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Enantioselective reductive amination: selected references for organometallic systems:
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47
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56449120814
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For a recent biocatalytic reductive animation see:
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For a recent biocatalytic reductive animation see:. Koszelewski D., Lavandera I., Clay D., Guebitz G.M., Rozzell, and Kroutil W. Angew. Chem., Int. Ed. 47 (2008) 9337
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Angew. Chem., Int. Ed.
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Koszelewski, D.1
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Clay, D.3
Guebitz, G.M.4
Rozzell5
Kroutil, W.6
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48
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67649600188
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note
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Kocovsky has already described a one pot procedure which involves the in situ preparation of imine followed by trichlorosilane-mediated reduction (see Ref. 7d). With those formammide-based catalysts it was shown that the ketone reduction was slower than imine reduction. However with our catalytic systems only a fine tuning of the experimental conditions allowed to efficiently perform the reductive amination process.
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50
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67649615706
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For two recent contributions about the enantioselective synthesis of β-amino acids involving the use of trichlorosilane see
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For two recent contributions about the enantioselective synthesis of β-amino acids involving the use of trichlorosilane see:
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51
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53849083142
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Malkov A.V., Stoncius S., Vrankova K., Arndt M., and Kocovsky P. Chem.-Eur. J. 14 (2008) 8082
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Kocovsky, P.5
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Zheng H.-J., Chen W.-B., Wu Z.-J., Deng J.-G., Lin W.-Q., Yuan W.-C., and Zhang X.-M. Chem.-Eur. J. 14 (2008) 9864
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Chem.-Eur. J.
, vol.14
, pp. 9864
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Zheng, H.-J.1
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Lin, W.-Q.5
Yuan, W.-C.6
Zhang, X.-M.7
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