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0001757279
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For recent, representative examples of our contribution, see, for example, the following: Binaphthyl-type ligands (a) Š. Vyskočil, J. Jaracz, M. Smrčina, M. Štícha, V. Hanuš, M. Polášek, and P. Kočovský J. Org. Chem. 63 1998 7727
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P. Kočovský, Š. Vyskočil, I. Císarová, J. Sejbal, I. Tišlerová, M. Smrčina, G.C. Lloyd-Jones, S.C. Stephen, C.P. Butts, M. Murray, and V. Langer J. Am. Chem. Soc. 121 1999 7714
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37
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0035249063
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Pyridine and bipyridine-type ligands: (g) A.V. Malkov, I.R. Baxendale, M. Bella, V. Langer, J. Fawcett, D.R. Russell, D.J. Mansfield, M. Valko, and P. Kočovský Organometallics 20 2001 673
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Malkov, A.V.1
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Langer, V.4
Fawcett, J.5
Russell, D.R.6
Mansfield, D.J.7
Valko, M.8
Kočovský, P.9
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39
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0037603215
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A.V. Malkov, D. Pernazza, M. Bell, M. Bella, A. Massa, F. Teplý, P. Meghani, and P. Kočovský J. Org. Chem. 68 2003 4727
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Bell, M.3
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Kočovský, P.8
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40
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0035862641
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For amino acid-based ligands, see Ref. 9 and the following: (j) A.V. Malkov, P. Spoor, V. Vinader, and P. Kočovský Tetrahedron Lett. 42 2001 509
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Malkov, A.V.1
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41
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0345614216
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For an overview of our earlier work, see: (k) P. Kočovský, A. Malkov, Š. Vyskočil, and G.C. Lloyd-Jones Pure Appl. Chem. 71 1999 1425
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3142759422
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0041878778
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Activation of other trichlorosilanes with Lewis basic organocatalysts has now been well established. For a review on chiral phosphoramides, see: (a) S.E. Denmark, and J. Fu Chem. Rev. 103 2003 2763
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(g) A.V. Malkov, M. Orsini, D. Pernazza, K.W. Muir, V. Langer, P. Meghani, and P. Kočovský Org. Lett. 4 2002 1047
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60
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0033569979
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For a related reduction of ketones, see: (b) F. Iwasaki, O. Onomura, K. Mishima, T. Maki, and Y. Matsumura Tetrahedron Lett. 40 1999 7507
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61
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28944444872
-
-
note
-
To obtain 14 in high yield, it is crucial to add NaH (in small portions) to a mixture of BOC-valine 13 and MeI. If the deprotonation of 13 is carried out prior to the addition of MeI, the methylation becomes inefficient.
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65
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M. Prushad, D. Har, B. Hu, H.Y. Kim, O. Repic, and T.J. Blacklock Org. Lett. 5 2003 125
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68
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0027953195
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Formamide 23b has been prepared previously as an oil: B.P. Coppola, M.C. Noe, D.J. Schwartz, R.L. Abdon, and B.M. Trost Tetrahedron 50 1994 93
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Tetrahedron
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Coppola, B.P.1
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Trost, B.M.5
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70
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0000598624
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For the use of N-Cbz (instead of N-BOC protection), see the following: (a) L. Aurelio, R.T.C. Brownlee, A.B. Hughes, and B.E. Sleebs Aust. J. Chem. 53 2000 425
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75
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28944437375
-
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note
-
3 was <5%, and ∼10% in MeCN.
-
-
-
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76
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23044461118
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See Ref. 12j and the following: (a) Malkov, A. V.; Bell, M.; Castelluzzo, F.; Kočovský, P. Org. Lett. 2005, 7, 3219.
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Malkov, A.V.1
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77
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28944437249
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Unpublished results
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(b) Malkov, A. V.; Stewart Liddon, A. J. P.; Bendová, L.; Haigh, D. Z.; Kočovský, P. Unpublished results
-
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Malkov, A.V.1
Stewart Liddon, A.J.P.2
Bendová, L.3
Haigh, D.Z.4
Kočovský, P.5
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79
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28944435993
-
-
note
-
While imines 1a-d,f,g,k all exists as pure (E)-isomers, NMR spectra of 1e,h indicate 11:1 and 14:1 (E/Z)-mixtures, respectively.
-
-
-
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80
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0032922728
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This strategy is commonly used in design of chiral selectors in chiral chromatography: W.H. Pirkle, and M.E. Koscho J. Chromatogr. A 840 1999 151
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Pirkle, W.H.1
Koscho, M.E.2
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81
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28944454223
-
-
note
-
3SiH shows two peaks at 21.69 and 21.76 ppm.
-
-
-
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82
-
-
28944448577
-
-
note
-
9
-
-
-
-
83
-
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28944443864
-
-
note
-
Preliminary experiments show striking conformational differences in the X-ray structures of several of these derivatives, which may lend further credence to this hypothesis. Details will be published in due course.
-
-
-
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84
-
-
28944436744
-
-
note
-
For the oxidative removal of the N-(p-methoxyphenyl) group to obtain the corresponding primary amine, see Ref. 2a.
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86
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P. Schnider, G. Koch, R. Prétôt, G. Wang, F.M. Bohnen, C. Krüger, and A. Pfaltz Chem. Eur. J. 3 1997 887
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0030928421
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W.H. Bunnelle, P.R. Singam, B.A. Narayanan, C.W. Bradshaw, and J.S. Liou Synthesis 1997 439
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98
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28944434265
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note
-
S retention times were swapped for 2a,b,d,g by mistake.
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