(S)-Methyl-2-acetamido-3-(3-chlorophenyl)-propanoate 19d
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1H-NMR (300 MHz, CDCl3): dH 1.98 (3 H, s), 3.04 (1 H, dd, J
13.9, 6.0), 3.13 (1 H, dd, J 13.9, 6.0), 3.72 (3 H, s), 4.85 (1 H,
apparent q, J 6.0), 6.20 (1 H, br s), 7.04 (2 H, d, J 8.0), 7.26 (2 H,
d, J 8.0); CSP-HPLC, CHIRALPAK IB 5 mm 250 ¥ 4.6 mm ID
column, heptane/ethanol 4 : 1, 1 mL min-1 showed 20% ee (tR
6.6 min, tS = 7.9 min).
=
3 D. R. Boyd, N. D. Sharma, L. Sbircea, D. Murphy, T. Belhocine, J.
F. Malone, S. L. James, C. C. R. Allen and J. T. G. Hamilton, Chem.
Commun., 2008, 5535.
1-Phenylethyl acetate 19e
4 D. R. Boyd, N. D. Sharma, L. Sbircea, D. Murphy, J. F. Malone, S. L.
James, C. C. R. Allen and J. T. G. Hamilton, Org. Biomol. Chem., 2010,
8, 1081.
5 L. Sbircea, N. D. Sharma, W. Clegg, R. W. Harrington, P. N. Horton,
M. B. Hursthouse, D. C. Apperley, D. R. Boyd and S. L. James, Chem.
Commun., 2008, 5538.
6 D. R. Boyd, N. D. Sharma, N. M. Llamas, C. R. O’Dowd and C. C. R.
Allen, Org. Biomol. Chem., 2007, 5, 2267.
7 D. R. Boyd, N. D. Sharma, M. Kaik, M. Bell, V. Berberian, P. Mc
Intyre, B. Kelly, C. Hardacre and P. J. Stevenson, Adv. Synth. Catal.,
2011, 353, 2455.
8 S. Kobayashi and K. Nishio, Tetrahedron Lett., 1993, 34, 3453.
9 S. E. Denmark, D. M. Coe, N. E. Pratt and B. D. Griedel, J. Org. Chem.,
1994, 59, 6161.
10 S. E. Denmark and J. P. Fu, Chem. Rev., 2003, 103, 2763; S. E. Denmark
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Jacobsen, Acc. Chem. Res., 2000, 33, 324.
1H-NMR (300 MHz, CDCl3): dH 1.54 (3 H, d, J 6.6), 2.07 (3 H, s),
5.88 (1 H, q, J 6.6), 7.26–7.49 (5 H, m); CSP-HPLC, CHIRALPAK
IB 5 mm 250 ¥ 4.6 mm ID column, heptane/ethanol 99 : 1, 0.5 mL
min-1 showed 40% ee (tR = 9.0 min, tS = 10.0 min).
Dimethyl 2-methylsuccinate 19f
1H-NMR (300 MHz, CDCl3): dH 1.22 (3 H, d, J 7.1), 2.41 (1 H, dd,
J 16.5, 7.1), 2.75 (1 H, dd, J 16.5, 7.1), 2.93 (1 H, apparent sextet,
J 7.1), 3.68 (3 H, s), 3.70 (3 H, s); CSP-HPLC, CHIRALPAK IB
5 mm 250 ¥ 4.6 mm ID column, heptane/ethanol 7 : 3, 1 mL min-1
showed 18% ee (tR = 5.7 min, tS = 6.8 min).
11 K. Iseki, S. Mizuno, Y. Kuroki and Y. Kobayashi, Tetrahedron Lett.,
1998, 39, 2767; K. Iseki, S. Mizuno, Y. Kuroki and Y. Kobayashi,
Tetrahedron, 1999, 55, 977.
Acknowledgements
Financial assistance was provided by an EU Marie Curie Host
Fellowship for Transfer of Knowledge, NOVACAT, project no.
29846 (K. S. D. and M. B.).
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14 C. Ogawa, M. Sugiura and S. Kobayashi, Angew. Chem., Int. Ed., 2004,
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