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129.44 (C-2+C-6), 134.10 (C-1), 148.41 (C-1¦), 152.65 (C-3+C-5), 161.65 (C(O)). Anal. calcd for
C23H26N2O6: C, 64.78; H, 6.15; N, 6.57; found: C, 64.56; H, 6.01; N, 6.39.
3.5.2. (1%S,2%R,5%R)-2%-(1-Methyl-1-phenylethyl)-5%-methylcyclohexyl 3,5-dinitrobenzoate 11
Yield 87%. Mp 126–128°C (cyclohexane–ether). [h]2D3 +164.0 (c 1.0, CHCl3). IR (KBr wmax
:
1
3090, 2970, 1717, 1654, 1627, 1549, 1458, 1343, 1280, 1168, 1076, 730, 718, 705 cm−1. H NMR
(CDCl3): 1.06–1.08 (d, 3H, J=7.28 Hz, 5%-CH3), 1.19 and 1.35 (2s, 6H, 8%-(CH3)2), 1.52–1.69 (m,
5H), 1.87–1.93 (m, 1H), 2.10–2.20 (m, 1H), 2.30–2.38 (m, 1H), 5.38–5.46 (d×t, 1H, Jt=10.31 Hz,
Jd=5.08 Hz, 1% -H), 6.57–6.62 (m, 1H, 4¦-H), 6.91–6.96 (m, 2H, 3¦-H+5¦-H), 7.21–7.25 (m, 2H,
ax
2¦-H+6¦-H), 8.44–8.45 (d, 2H, J=2.21 Hz, 2-H+6-H), 9.18–9.19 (t, 1H, Jt=4.25 Hz, Jd=2.18
Hz, 4-H). 13C NMR (CDCl3): 18.54 (C-7%), 21.35 (C-3%), 21.77 (C-5%), 28.21 (C-9%), 31.24 (C-10%),
31.51 (C-4%), 39.01 (C-6%), 39.92 (C-8%), 51.47 (C-2%), 73.98 (C-1%), 122.14 (C-4), 124.77 (C-4¦),
125.47 (C-2¦+C-6¦), 128.40 (C-3¦+C-5¦), 129.45 (C-2+C-6), 134.17 (C-1), 148.42 (C-1¦), 152.39
(C-3+C-5), 161.61 (C(O)). Anal. calcd for C23H26N2O6: C, 64.78; H, 6.15; N, 6.57; found: C,
64.98; H, 6.34; N, 6.70.
3.5.3. (1%S,2%S,5%R)-2%-(1-Methyl-1-phenylethyl)-5%-methylcyclohexyl 3,5-dinitrobenzoate 12
Yield 77%. Mp 139–140°C (cyclohexane–ether). [h]2D3 +116.8 (c 1.0, CHCl3). IR (KBr wmax
:
3112, 2954, 1719, 1654, 1629, 1548, 1497, 1457, 1342, 1276, 1170, 1119, 1072, 730, 718, 705 cm−1.
1H NMR (CDCl3): 0.83–0.86 (d, 3H, J=7.56 Hz, 5%-CH3), 1.02–1.25 (m, 2H), 1.36 and 1.41 (2s,
6H, 8%-(CH3)2), 1.58–1.99 (m, 6H), 5.45 (a.s., 1H, 1% -H), 6.88–6.93 (t, 1H, 4¦-H), 7.08–7.13 (t,
eq
2H, 3¦-H+5%-H), 7.23–7.25 (d, 2H, J=7.48 Hz, 2¦-H+6¦-H), 8.82–8.83 (d, 2H, J=2.12 Hz,
2-H+6-H), 9.17–9.18 (t, 1H, Jt=4.23 Hz, Jd=2.11 Hz, 4-H). 13C NMR (CDCl3): 22.29 (C-3%),
23.26 (C-7%), 26.30 (C-5%), 27.51 (C-9%), 27.88 (C-10%), 35.65 (C-4%), 40.19 (C-6%), 40.34 (C-8%),
52.19 (C-2%), 74.27 (C-1%), 122.47 (C-4), 125.76 (C-4¦), 126.63 (C-2¦+C-6¦), 128.40 (C-3¦+C-5¦),
129.52 (C-2+C-6), 134.80 (C-1), 148.40 (C-1¦), 148.87 (C-3+C-5), 161.71 (C(O)). Anal. calcd for
C23H26N2O6: C, 64.78; H, 6.15; N, 6.57; found: C, 64.93; H, 6.19; N, 6.36.
3.5.4. (1%R,2%R,5%R)-2%-(1-Methyl-1-phenylethyl)-5%-methylcyclohexyl 3,5-dinitrobenzoate 13
Yield 74%. Mp 160–161°C (cyclohexane–ether). [h]2D3 −102.4 (c 1.0, CHCl3). IR (KBr wmax
:
3093, 2981, 2953, 2905, 1721, 1631, 1598, 1542, 1497, 1458, 1382, 1343, 1274, 1172, 1115, 1072,
923, 730, 719, 703 cm−1. 1H NMR (CDCl3): 0.92–0.94 (d, 3H, J=7.38 Hz, 5%-CH3), 1.37 and 1.42
(2s, 6H, 8%-(CH3)2), 1.58–2.07 (m, 8H), 5.40 (a.s., 1H, 1% -H), 6.90–6.95 (t, 1H, 4¦-H), 7.08–7.13
eq
(t, 2H, 3¦-H+5%-H), 7.22–7.25 (d, 2H, 2¦-H+6¦-H), 8.83–8.84 (d, 2H, J=2.18 Hz, 2-H+6-H),
9.18–9.19 (t, 1H, Jt=4.15 Hz, Jd=2.19 Hz, 4-H). 13C NMR (CDCl3): 18.17 (C-3%), 21.16 (C-7%),
26.29 (C-5%), 27.72 (C-9%), 27.91 (C-10%), 32.40 (C-4%), 36.97 (C-6%), 40.34 (C-8%), 52.35 (C-2%),
74.75 (C-1%), 122.47 (C-4), 125.78 (C-4¦), 126.63 (C-2¦+C-6¦), 128.39 (C-3¦+C-5¦), 129.52
(C-2+C-6), 134.73 (C-1), 148.39 (C-1¦), 148.92 (C-3+C-5), 161.74 (C(O)). Anal. calcd for
C23H26N2O6: C, 64.78; H, 6.15; N, 6.57; found: C, 64.95; H, 6.41; N, 6.38.
Acknowledgements
The authors would like to thank the Spanish Ministry of Education and Science (MEC-
DGICYT, PB94-0617) and the Xunta de Galicia (XUGA 20307B94) for financially supporting
this work.