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note
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[19a,][20a,b,d]
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85
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33746707248
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note
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Note that an examination of 3-octanone failed to provide a reasonable de (< 10%).
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86
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33746727389
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note
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[20f] for comparative data.
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87
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33746717218
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note
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Not examined were the following two possible solutions: 1) once the reductive amination reaction is complete, raise the hydrogen pressure to facilitate complete hydrogenolysis, or 2) for Raney-Ni or Pt-C ketones we never examined the possibility of completing the reductive amination reaction, and then simply adding Pd-C and continuing the hydrogenation to enable a one-pot (ketone to primary amine) reductive amination-hydrogenolysis sequence.
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(Ed.: K. G. Gadamasetti), Marcel Dekker, New York
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We recently became aware of Pd-C catalysts specifically for debenzylations and suppression of racemization, this may be helpful for this hydrogenolysis, see: V. Farina, K. Grozinger, H. Müller-Bötticher, G. P. Roth, Ontazolast: The Evolution of a Process, in: Process Chemistry in the Pharmaceutical Industry, (Ed.: K. G. Gadamasetti), Marcel Dekker, New York, 1999, pp. 107-124.
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98
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33746721824
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[20g]
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[20g]
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-
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99
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33746688258
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note
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For example, for the use of chiral Lewis acid equivalents in combination with prochiral ketones and amines for enantioselective reductive amination, or as a starting point for the investigation of achiral Lewis acid derivatives thereof in the search for enhanced de and/or reaction rate with α-MBA or other amines.
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