M. J. Alves et al. / Tetrahedron Letters 47 (2006) 7595–7597
4. (a) Zhu, X.-F. Nucleosides, Nucleotides and Nucleic Acids
7597
(dd, 1H, J = 5.6, 1.7 Hz), 6.46 (dd, 1H, J = 4.5, 3.3 Hz),
7.19–7.31 (m, 5H). Compound (1c): 0.99 (s, 9H), 1.26 (d,
1H, J = 8.4 Hz), 1.57 (d, 1H, J = 8.4 Hz), 1.86 (dd, 1H,
J = 9.2 Hz, 5.1 Hz), 2.93 (s, 1H), 3.12 (d, 1H, J = 9.3 Hz),
3.18 (d, 1H, J = 9.3 Hz), 3.28–3.44 (m, 2H), 3.66 (s, 1H),
6.09–6.13 (m, 1H), 6.40–6.45 (m, 1H), 7.10–7.50 (m, 15H).
Compound (1d): 0.89 (s, 9H), 1.19–1.26 (m, 2H), 1.32 (d,
3H, J = 6.6 Hz), 1.87–1.92 (m, 1H), 2.98–3.09 (m, 4H),
4.09 (br, 1H), 6.17 (dd, 1H, J = 5.4, 2.1 Hz), 6.44–6.48 (m,
1H), 7.10–7.50 (m, 15H). Compound (1e): 1.36–1.39 (d,
1H, Janti = 8.4 Hz), 1.37 (d, 3H, J = 6.9 Hz), 1.64 (d, 1H,
Jsyn = 8.4 Hz), 1.87–1.91 (m, 1H), 2.76 (dd, 1H,
J = 9.9 Hz, 3.6 Hz), 2.91 (s, 1H), 2.94 (d, 1H, J =
9.9 Hz), 3.03 (q, 1H, J = 6.6 Hz), 4.08 (d, 2H,
J = 4.8 Hz), 4.13 (s, 1H), 6.20 (dd, 1H, J = 5.4 Hz,
2.1 Hz), 6.40–6.42 (m, 1H), 7.08–7.28 (m, 10H). Com-
pound (1f): 1.38 (d, 1H, J = 6.5 Hz), 1.40 (s, 1H), 1.50–
1.45 (m, 1H), 1.70 (d, 1H, J = 8.8 Hz), 1.89 (s, 3 H), 2.75
(s, 1H), 3.05 (q, 1H, J = 6.5 Hz), 3.33 (dd, 1H, J = 4.2 Hz,
11.1 Hz), 3.56 (t, 1H, J = 10.8 Hz), 4.19 (s, 1H), 6.21 (d,
1H, J = 5.1 Hz), 6.39–6.44 (m, 1H), 7.20–7.50 (m, 5H).
Compound (3a): 1.74 (s, 1H), 2.28 (s, 1H), 2.44 (s, 1H),
2.62 (s, 1H), 3.27 (d, 1H, J = 3.8 Hz), 3.63 (s, 3H), 3.52–
4.22 (m, 6H), 7.21–7.34 (m, 5H). Compound (3c): 1.02 (s,
9H), 1.49 (d, 1H, J = 10.6 Hz), 1.62 (d, 1H, J = 10.6 Hz),
2.15 (t, 1H, J = 6.9 Hz), 2.39 (s, 1H), 2.93 (s, 1H), 3.31 (d,
2H, J = 7.1 Hz), 3.61 (d, 2H, J = 2.6 Hz), 3.83 (d, 1H,
J = 5.4 Hz), 4.23 (d, 1H, J = 5.7 Hz), 4.41 (s, 2H), 7.18–
7.30 (m, 5H), 7.34–7.69 (m, 10H). Compound (3d): 0.88 (s,
9H), 1.34 (d, 3H, J = 6.6 Hz), 1.49 (d, 1H, J = 10.8 Hz),
1.69 (d, 1H, J = 10.8 Hz), 2.14 (dd, 1H, J = 9.9 Hz,
4.2 Hz), 2.47 (s, 1H), 2.53 (dd, 1H, J = 10.1 Hz, 4.1 Hz),
2.84 (t, 1H, J = 10.1 Hz), 2.89 (s, 2H), 3.38 (s, 1H), 3.46 (q,
1H, J = 6.6 Hz), 3.87 (d, 1H, J = 6.0 Hz), 4.27 (d, 1H,
J = 6.0 Hz), 7.09–7.45 (m, 15H). Compound (3e): 1.38 (d,
3H, J = 6.6 Hz), 1.49 (d, 1H, J = 10.7 Hz), 1.65 (d, 1H,
J = 10.7 Hz), 2.50 (s, 1H), 2.64 (m, 1H), 2.78 (dd, 1H,
J = 9.9 Hz, 4.2 Hz), 2.89 (s, 2H), 2.96 (dd, 1H, J = 9.9 Hz,
4.1 Hz), 3.24 (q, 1H, J = 6.6 Hz), 3.39 (s, 1H), 3.90 (d, 1H,
J = 6.1 Hz), 4.11 (d, 2H, J = 5.0 Hz), 4.28 (d, 1H,
J = 6.1 Hz), 7.09–7.31 (m, 10H). Compound (3f): 1.37
(d, 1H, J = 6.5 Hz), 1.74 (s, 1H), 1.88 (s, 3H), 2.27 (s, 1H),
2.39 (s, 1H), 2.59 (s, 1H), 3.02 (q, 1H, J = 6.5 Hz), 3.30 (m,
1H), 3.32–4.21 (m, 6H), 7.23–7.51 (m, 5H). Compound
(7a): 1.19–1.75 (m, 2H), 2.25–2.36 (m, 2H), 2.43–2.71 (s,
2H), 3.45–3.96 (m, 10H), 7.23–7.30 (m, 5H). Compound
(7c): 1.05 (s, 9H), 1.99 (s, 2H), 2.18–2.26 (m, 1H), 2.40–
2.53 (m, 1H), 2.74 (dd, 1H, J = 17.1 Hz, 9.6 Hz), 3.28 (q,
1H, J = 3.3 Hz), 3.37–3.55 (m, 2H), 3.61–3.72 (m, 4H),
3.89 (s, 2H), 4.94 (d, 1H, J = 15 Hz), 6.95–7.65 (m, 15H).
Compound (7d): 1.06 (s, 9H), 1.25 (d, 3H, J = 6.6 Hz),
1.61–1.67 (m, 1H), 2.21–2.33 (m, 1H), 2.35 (s, 2H), 2.83
(dd, 1H, J = 11.1 Hz, 4.2 Hz), 3.01 (dd, 1H, J = 11.4 Hz,
2.1 Hz), 3.12 (m, 1H), 3.30 (dd, 1H, J = 7.0 Hz, 3.2 Hz),
3.57–3.77 (m, 4H), 3.84 (q, 1H, J = 6.6 Hz), 7.18–7.30 (m,
5H), 7.34–7.69 (m, 10H). Compound (7e): 1.44 (d, 3H,
J = 6.6 Hz), 1.55–1.62 (m, 1H), 2.22–2.31 (m, 2H), 2.60 (s,
2H), 2.90 (dd, 1H, J = 11.2 Hz, 4.1 Hz), 3.05 (dd, 1H,
J = 11.4 Hz, 2.4 Hz), 3.10–3.20 (m, 1H), 3.39–3.42 (m,
1H), 3.46–3.68 (m, 4H), 3.94 (q, 1H, J = 6.6 Hz), 4.46–
4.54 (m, 2H), 7.20–7.40 (m, 10H). Compound (7f): 1.45 (d,
3H, J = 7.4 Hz), 1.66 (dd, 1H, J = 14.8 Hz, 1.9 Hz), 2.05
(s, 3H), 2.10–2.12 (s, 1H), 2.20–2.32 (m, 1H), 2.83 (dd, 1H,
J = 11.1 Hz, 4.2 Hz), 3.00 (d, 1H, J = 10.2 Hz), 3.10–3.15
(m, 1H), 3.36–3.43 (m, 1H), 3.55–3.65 (m, 2H), 3.90–4.10
(m, 2H), 4.25 (dd, 1H, J = 11.6 Hz, 3.2 Hz), 4.70 (s, 2H),
7.24–7.30 (m, 5H).
´
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F.; Lopes, V. H. C.; Magalhaes, A. L.; Cordeiro, M. N. D.
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S. Tetrahedron 2005, 61, 10951, and references cited therein;
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12. Comparison of the spectroscopic data (1H and 13C NMR)
and specific rotation of aminoalcohol (ꢀ)-9b with an
authentic sample of (+)-9b, whose absolute configuration
is well known from its crystallographic X-ray data (CCDC
240700) allowed the determination of its absolute config-
uration (1S, 3exo), and therefore the configuration of its
derivatives 3d–g (also 1S, 3exo) and 7d–g (2S,3S,5S) could
be established.
25
13. (a) The recovered alcohol [½aꢁD ꢀ25.2 (c 0.5, CHCl3)], was
identified as (ꢀ)-8-phenylmenthol by comparison of its
spectroscopic and specific rotation data with those
reported in the literature.13b (b) Fernandez, F.; Garcıa-
´
´
´
´
´
Mera, X.; Lopez, C.; Rodrıguez, G.; Rodrıguez-Borges, J.
E. Tetrahedron: Asymmetry 2000, 11, 4805.
´
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14. Garcıa, M. D.; Caamano, O.; Fernandez, F.; Abeijon, P.;
˜
Blanco, J. M. Synthesis 2006, 1, 73–80.
15. Selected H NMR data [dH (300 MHz, CDCl3)]:
1
Compound (9b): 1.32–1.40 (m, 1H), 1.39 (d, 3H,
J = 6.5 Hz), 1.72–1.80 (m, 2H), 2.01 (s, 1H), 2.70–2.76
(m, 2H), 2.99–3.08 (m, 2H), 4.14 (d, 1H, J = 1.3 Hz), 6.20
16. Bailey, P. D.; McDonald, I. M.; Rosair, G. M.; Taylor, D.
J. Chem. Soc. Chem. Commun. 2000, 2451.