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The condensation of a range of aniline derivatives with a range of aldehydes is known to give the corresponding (ZT)-configured imines with good to excellent levels of diastereoselectivity; see: Tennant, G. Comprehensive Organic Chemistry; Barton, D. E, Ollis, W. D, Eds, Pergamon: Oxford, 1979; 2, Chapter 8. Patai, S. The Chemistry of the Carbon- Nitrogen Double Bond; John Wiley and Sons: Chichester, 1970. For some very recent examples, see: Shen, M, Driver, T. G. Org. Lett. 2008, 10, 3367
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The condensation of a range of aniline derivatives with a range of aldehydes is known to give the corresponding (ZT)-configured imines with good to excellent levels of diastereoselectivity; see: Tennant, G. Comprehensive Organic Chemistry; Barton, D. E., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, Chapter 8. Patai, S. The Chemistry of the Carbon- Nitrogen Double Bond; John Wiley and Sons: Chichester, 1970. For some very recent examples, see: Shen, M.; Driver, T. G. Org. Lett. 2008, 10, 3367.
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69
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54249133375
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Albert, J.; D'Andrea, L.; Bautista, J.; Gonzalez, A.; Granell, J.; Font- Bardia, M.; Calvet, T. Organometallics 2008, 27, 5108.
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(2008)
Organometallics
, vol.27
, pp. 5108
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Albert, J.1
D'Andrea, L.2
Bautista, J.3
Gonzalez, A.4
Granell, J.5
Font- Bardia, M.6
Calvet, T.7
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70
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66149118528
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The parent amine (K)-N-benzyl-N-(a-methylbenzyl)amine was assessed to be >98% ee by 1H NMR chiral shift experiments using (S)- O-acetylmandelic acid and comparison with an authentic racemic sample.
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The parent amine (K)-N-benzyl-N-(a-methylbenzyl)amine was assessed to be >98% ee by 1H NMR chiral shift experiments using (S)- O-acetylmandelic acid and comparison with an authentic racemic sample.
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71
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66149094585
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Given the known enantiomeric purity (i.e., >98% ee) of the lithium amide (R)-4 used to initiate the tandem conjugate addition/cyclization process, the enantiomeric purity of 15, 16, and 22-27 was assigned from the diastereoisomeric purity (determined by peak integration of the 1H NMR spectrum of the crude reaction mixture and the pure product).
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Given the known enantiomeric purity (i.e., >98% ee) of the lithium amide (R)-4 used to initiate the tandem conjugate addition/cyclization process, the enantiomeric purity of 15, 16, and 22-27 was assigned from the diastereoisomeric purity (determined by peak integration of the 1H NMR spectrum of the crude reaction mixture and the pure product).
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72
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66149140518
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(R)-N-tert-Butoxycarbonyl-N-benzyl-N-(a- methylbenzyl)amine, formed by reaction of the excess lithium amide (R)-4 with (Boc)2O, was also isolated.
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(R)-N-tert-Butoxycarbonyl-N-benzyl-N-(a- methylbenzyl)amine, formed by reaction of the excess lithium amide (R)-4 with (Boc)2O, was also isolated.
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73
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0028126511
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Costello, J. F.; Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1994, 5, 1999.
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(1999)
Tetrahedron: Asymmetry
, vol.1994
, pp. 5
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Costello, J.F.1
Davies, S.G.2
Ichihara, O.3
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74
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37049072443
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Davies, S. G.; Garrido, N. M.; Ichihara, O.; Walters, I. A. S. Chem. Commun. 1993, 1153.
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(1993)
Chem. Commun
, pp. 1153
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Davies, S.G.1
Garrido, N.M.2
Ichihara, O.3
Walters, I.A.S.4
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76
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37049081663
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Davies, S. G.; Ichihara, O.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1141.
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(1994)
J. Chem. Soc., Perkin Trans. 1
, pp. 1141
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Davies, S.G.1
Ichihara, O.2
Walters, I.A.S.3
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77
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37049079385
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Bunnage, M. E.; Chernega, A. N.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2373.
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(1994)
J. Chem. Soc., Perkin Trans. 1
, pp. 2373
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Bunnage, M.E.1
Chernega, A.N.2
Davies, S.G.3
Goodwin, C.J.4
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78
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The remarkable resistance of, aryl, amino ester derivatives to undergo cleavage of the N-C(3) bond has been attributed to the presence of an intramolecular hydrogen bond between the, amino substituents and the carbonyl oxygen atom that holds the C(3)-aryl group in a conformation that disfavors hydrogenolysis of the benzylic N-C(3) bond; see ref 8a
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The remarkable resistance of /?-aryl-/?-amino ester derivatives to undergo cleavage of the N-C(3) bond has been attributed to the presence of an intramolecular hydrogen bond between the /?-amino substituents and the carbonyl oxygen atom that holds the C(3)-aryl group in a conformation that disfavors hydrogenolysis of the benzylic N-C(3) bond; see ref 8a.
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