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note
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The reduction of acetophenone with other prominent ligands reported in Table 1 resulted in the following conversion and enantioselectivity after 30 minutes reaction time: V-(S)-4, 65% conv. 97% ee; I-(S)-4, 72% conv. 97% ee.
-
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61
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0346636472
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note
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A-(rac)-4 is the 1:1 diastereomeric mixture of ligands A-(S)-4 and A-(R)-4. This compound was prepared from L-alanine and racemic 1-amino-2-propanol.
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68
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a) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297-300; Angew. Chem. Int. Ed. Engl. 1997, 36, 285-288;
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b) M. Yamakawa, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466-1478;
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c) R. Noyori, M. Yamakawa, S. Hashiguchi, J. Org. Chem. 2001, 66, 7931-7944.
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Noyori, R.1
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For other recent mechanistic discussions, see: a) D. A. Alonso, P. Brandt, S. J. M. Nordin, P. G. Andersson, J. Am. Chem. Soc. 1999, 121, 9580-9588;
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b) D. G. I. Petra, J. N. H. Reek, J.-W. Handgraaf, E. J. Meijer, P. Dierkes, P. C. J. Kamer, J. Brussee, H. E. Schoemaker, P. W. N. M. van Leeuwen, Chem. Eur. J. 2000, 6, 2818-2829;
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Petra, D.G.I.1
Reek, J.N.H.2
Handgraaf, J.-W.3
Meijer, E.J.4
Dierkes, P.5
Kamer, P.C.J.6
Brussee, J.7
Schoemaker, H.E.8
Van Leeuwen, P.W.N.M.9
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f) J.-W. Handgraaf, J. N. H. Reek, E. J. Meijer, Organometallics 2003, 22, 3150-3157.
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Organometallics
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Handgraaf, J.-W.1
Reek, J.N.H.2
Meijer, E.J.3
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77
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0346005335
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For GLC conditions and retention times, see; ref. [4b]
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For GLC conditions and retention times, see; ref. [4b].
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