R. J. Abdel-Jalil et al. / Tetrahedron Letters 42 (2001) 2435–2437
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1H, H-1), 4.25 (dd, J=2.4, 12.8 Hz, 1H, H-5), 4.03 (m,
1H, H-4), 3.67 (dd, J=7.3, 9.8 Hz, 1H, H-2), 3.62 (dd,
J=3.4, 12.2 Hz, 1H, H-5%), 3.43 (dd, J=6.1, 9.8 Hz, 1H,
H-3). lC (63 MHz, CDCl3): 52.1 (C-3), 64.7 (C-4), 64.6
(C-5), 70.6 (OCH2Ph), 73.3 (C-2), 102.2 (C-1), 121.4,
124.4, 128.1–129.1, 137.0, 143.3 (C6H5, C6H5%), 162.2 (C-
7). FAB-MS: m/z=357.1 [M++1]. Data for 3b; [h]D20=
15. Data for 6a; [h]D20=+135.2° (c=0.16, CH2Cl2); H NMR
(250 MHz, CDCl3): lH 6.87–7.40 (m, 10H, C6H5, C6H5),
4.9 (d, J=3.4 Hz, 1H, H-1), 4.77 (d, J=11.9 Hz, 1H,
OCHHPh), 4.69 (bs, 1H, N-H), 4.53 (d, J=11.6 Hz, 1H,
OCHHPh), 4.05 (m, 1H, H-4), 3.92 (m, 2H, H5, H5%), 3.76
(dd, J=3.7, 9.8 Hz, 1H, H-2), 3.59 (dd, J=5.5, 9.8 Hz,
1H, H-3). Data for 6b; [h]2D0=+137.1° (c=0.25, CH2Cl2);
1H NMR (250 MHz, CDCl3): lH 7.27–7.38 (m, 5H,
C6H5), [7.20 (d, J=8.9 Hz, 2H), 6.99 (d, J=8.9 Hz, 2H),
C6H4], 5.38 (bs, 1H, N-H), 4.87 (d, J=3.4 Hz, 1H, H-1),
4.74 (d, J=11.6 Hz, 1H, OCHHPh), 4.49 (d, J=11.6 Hz,
1H, OCHHPh), 3.91 (bd, J=4.0 Hz, 1H, H-4), 3.66–3.84
(m, 3H, H-5, H-5%, H-2), 3.52 (dd, J=5.2, 9.8 Hz, 1H,
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−60.9° (c=0.14, CH2Cl2); H NMR (250 MHz, CDCl3):
lH 7.26–7.30 (m, 5H, C6H5), [7.08 (d, J=8.9 Hz, 2H),
7.16 (d, J=8.9 Hz, 2H), (C6H4)], 4.85 (d, J=11.6 Hz, 1H,
OCHHPh), 4.53 (d, J=11.3 Hz, 1H, OCHHPh), 4.25 (m,
1H, H-5), 4.24 (d, J=7.3 Hz, 1H, H-1), 4.10 (m, 1H,
H-4), 3.67 (dd, J=3.1, 12.8 Hz, 1H, H-5%), 3.62 (dd,
J=7.9, 9.2 Hz, 1H, H-2), 3.38 (dd, J=5.8, 9.8 Hz, 1H,
H-3). Data for 3c; [h]2D0=−68.6° (c=0.1, CH2Cl2); 1H
NMR (250 MHz, CDCl3): lH 7.29–7.36 (m, 5H, C6H5),
6.87–7.07 (m, 4H, C6H4), 4.89 (d, J=11.6 Hz, 1H,
OCHHPh), 4.59 (d, J=11.6 Hz, 1H, OCHHPh), 4.30 (d,
J=7.3 Hz, 1H, H-1), 4.08 (bd, J=12.8 Hz, 1H, H-5),
3.90 (bs, 1H, H-4), 3.68 (dd, J=7.6, 9.8 Hz, 1H, H-2),
3.58 (dd, J=1.8, 12.5 Hz, 1H, H-5%), 3.38 (dd, J=5.8, 9.5
Hz, 1H, H-3). Data for 3d; [h]2D0=−80.0° (c=0.05,
H-3). Data for 6c; [h]2D0=+156.8° (c=0.21, CH2Cl2); H
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NMR (250 MHz, CDCl3): lH 7.29–7.39 (m, 5H, C6H5),
6.89–7.08 (m, 4H, C6H4), 5.09 (bs, 1H, N-H), 4.92 (d,
J=3.4 Hz, 1H, H-1), 4.77 (d, J=11.6 Hz, 1H,
OCHHPh), 4.52 (d, J=11.6 Hz, 1H, OCHHPh), 3.99
(bd, J=4.6 Hz, 1H, H-4), 3.81–3.90 (m, 2H, H-5, H-5%),
3.78 (dd, J=3.4, 9.8 Hz, 1H, H-2), 3.55 (dd, J=5.2, 9.8
Hz, 1H, H-3). Data for 6d; [h]2D0=+113.8° (c=0.18,
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CH2Cl2); H NMR (250 MHz, CDCl3): lH 7.21–7.30 (m,
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CH2Cl2); H NMR (250 MHz, CDCl3): lH 7.29–7.35 (m,
5H, C6H5), [6.98 (d, J=8.9 Hz, 2H), 6.74 (d, J=8.8 Hz,
2H), C6H4], 4.85 (d, J=3.4 Hz, 1H, H-1), 4.70 (d, J=
11.9 Hz, 1H, OCHHPh), 4.46 (d, J=11.6 Hz, 1H,
OCHHPh), 3.93 (bd, J=5.2 Hz, 1H, H-4), 3.81 (bs, 2H,
H-5, H-5%), 3.71 (dd, J=9.5, 3.7 Hz, 1H, H-2), 3.70 (s,
3H, C6H4OCH3), 3.49 (dd, J=9.8, 5.5 Hz, 1H, H-3).
5H, C6H5), [6.74 (d, J=8.9 Hz, 2H), 7.01 (d, J=8.9 Hz,
2H), C6H4], 5.61 (bs, 1H, N-H), 4.86 (d, J=11.6 Hz, 1H,
OCHHPh), 4.58 (d, J=11.6 Hz, 1H, OCHHPh), 4.29 (d,
J=7.3 Hz, 1H, H-1), 4.07 (dd, J=2.4, 12.8 Hz, 1H, H-5),
3.90 (m, 1H, H-4), 3.66 (dd, J=7.3, 9.5 Hz, 1H, H-2),
3.53 (dd, J=3.4, 12.8 Hz, 1H, H-5%), 3.36 (dd, J=6.1, 9.5
Hz, 1H, H-3). Data for 3e; [h]2D0=−96.8° (c=0.06,
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Data for 6e; [h]2D0=+124.9° (c=0.28, CH2Cl2); H NMR
(250 MHz, CDCl3): lH 7.27–7.39 (m, 5H, C6H5), [7.06 (d,
J=8.2 Hz, 2H), 6.99 (d, J=8.4 Hz, 2H), C6H4], 5.01 (bs,
1H, N-H), 4.89 (d, J=3.4 Hz, 1H, H-1), 4.75 (d, J=11.6
Hz, 1H, OCHHPh), 4.51 (d, J=11.6 Hz, 1H, OCHHPh),
3.95 (bd, J=5.2 Hz, 1H, H-4), 3.83 (bs, 2H, H-5, H-5%),
3.76 (dd, J=3.4, 9.8 Hz, 1H, H-2), 3.54 (dd, J=5.2, 9.8
Hz, 1H, H-3), 2.29 (s, 3H, C6H4CH3).
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CH2Cl2); H NMR (250 MHz, CDCl3): lH 7.31–7.36 (m,
5H, C6H5), [7.05 (d, J=8.9 Hz, 2H), 7.10 (d, J=8.9 Hz,
2H), C6H4], 4.90 (d, J=11.6 Hz, 1H, OCHHPh), 4.59 (d,
J=11.6 Hz, 1H, OCHHPh), 4.31 (d, J=7.3 Hz, 1H,
H-1), 4.27 (m, 1H, H-5), 4.08 (m, 1H, H-4), 3.69 (m, 2H,
H-2, H-5%), 3.43 (dd, J=5.8, 9.8 Hz, 1H, H-3).
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