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(m, 1H), 2.46 (dt, JZ10.2, 6.0 Hz, 1H), 2.65 (dd, JZ14.1,
6.0 Hz, 1H), 2.72 (dd, JZ10.2, 14.1 Hz, 1H), 3.64 (dt, JZ
10.2, 2.7 Hz, 1H), 3.83 (dt, JZ2.7, 11.1 Hz, 1H), 5.22 (d,
JZ3.6 Hz, 1H), 7.18–7.32 (m, 5H); 13C NMR (CDCl3) For
major isomer: d 20.22, 21.89, 24.33, 20.35, 35.00, 44.10,
46.35, 64.34, 84.84, 100.55, 126.12, 128.38 (2C), 128.79
(2C), 140.38, for minor isomer: d 20.24, 23.38, 25.57, 30.94,
31.62, 38.04, 51.03, 60.67, 79.35, 98.66, 126.13, 128.50
(2C), 128.56 (2C), 140.61. Found: C, 77.91; H, 9.24%.
Calcd for C16H22O2: C, 78.01; H, 9.00%.
(d, JZ8.1 Hz, 2H), 7.05 (d, JZ8.1 Hz, 2H), 7.16–7.33 (m,
5H), 7.69 (d, JZ8.1 Hz, 2H); 13C NMR (CDCl3) d 21.32,
30.89, 38.87, 40.22, 47.25, 52.66, 126.28, 127.49 (2C),
128.47 (2C), 128.58 (2C), 129.64 (2C), 133.89, 139.74,
143.37. Found: C, 68.28; H, 6.69; N, 4.36%. Calcd for
C18H21O2NS: C, 68.54; H, 6.71; N, 4.44%.
4.5.8. trans-3-Benzyl-1-oxa-2-pentylcyclopentane (6b).
IR (neat) 3022, 2922, 2854, 1604, 1496, 1455, 1380,
1
1110, 1078, 1032, 1007, 905, 743, 698 cmK1; H NMR
(CDCl3) d 0.87 (t, JZ6.75 Hz, 3H), 1.19–1.48 (m, 8H),
1.57–1.68 (m, 1H), 1.89–2.11 (m, 2H), 2.54 (dd, JZ9.3,
13.5 Hz, 1H), 2.78 (dd, JZ5.7, 13.5 Hz, 1H), 3.49–3.55 (m,
1H), 3.80 (dd, JZ6.2, 7.4 Hz, 2H), 7.15–7.32 (m, 5H); 13C
NMR (CDCl3) d 13.90, 22.47, 25.93, 31.81, 32.41, 34.62,
39.25, 46.10, 66.62, 84.15, 126.07, 128.42 (2C), 128.85
(2C), 140.80. Found: C, 82.72; H, 10.61%. Calcd for
C16H24O: C, 82.70; H, 10.41%.
4.5.3. 7-Benzyl-7-methyl-2,9-dioxabicyclo[4.3.0]nonane
(4d). IR (neat) 2920, 2862, 1604, 1496, 1453, 1411, 1381,
1278, 1245, 1137, 1084, 1049, 1022, 964, 942, 895, 754,
701 cmK1; 1H NMR (CDCl3) d 0.98 (s, 3H), 1.52–1.79 (m,
4H), 1.90–2.00 (m, 1H), 2.62 (d, JZ13.5 Hz, 1H), 2.85 (d,
JZ13.5 Hz, 1H), 3.40 (d, JZ8.1 Hz, 1H), 3.60–3.82 (m,
2H), 4.13 (d, JZ8.1 Hz, 1H), 5.45 (d, JZ3.9 Hz, 1H),
7.11–7.31 (m, 5H); 13C NMR (CDCl3) d 21.26, 23.03,
23.84, 40.16, 44.18, 44.55, 61.15, 76.13, 101.76, 126.24,
128.21 (2C), 129.92 (2C), 138.58. Found: C, 77.36; H,
8.80%. Calcd for C15H20O2: C, 77.55; H, 8.58%.
4.5.9. 1-Cyclopentylmethyl-4-methoxybenzene (6c). IR
(neat) 2946, 2862, 1613, 1584, 1513, 1464, 1299, 1246,
1177, 1039, 829, 806, 748 cmK1; 1H NMR (CDCl3) d 1.12–
1.24 (m, 2H), 1.42–1.75 (m, 6H), 1.99–2.09 (m, 1H), 2.54
(d, JZ7.5 Hz, 2H), 3.78 (s, 3H), 6.82 (d, JZ8.7 Hz, 2H),
7.08 (d, JZ8.7 Hz, 2H); 13C NMR (CDCl3) d 24.83 (2C),
32.30 (2C), 41.07, 42.10, 55.15, 113.57 (2C), 129.70 (2C),
134.61, 157.71. Found: C, 82.12; H, 9.72%. Calcd for
C13H18O: C, 82.06; H, 9.53%.
4.5.4. 7-Benzyl-2,9-dioxabicyclo[4.3.0]nonane (4e). IR
(neat) 2916, 1604, 1492, 1453, 1404, 1251, 1136, 1021,
1
947, 903, 750, 699 cmK1; H NMR (CDCl3) For major
isomer: d 1.50–1.67 (m, 3H), 1.72–1.81 (m, 1H), 1.92–2.01
(m, 1H), 2.58–2.78 (m, 3H), 3.61–3.68 (m, 1H), 3.77 (t, JZ
9.0 Hz, 2H), 3.88 (t, JZ7.5 Hz, 1H), 5.28 (d, JZ3.9 Hz,
1H), 7.15–7.31 (m, 5H); 13C NMR (CDCl3) For major
isomer: d 19.42, 23.02, 33.26, 36.46, 42.41, 60.91, 69.82,
101.97, 126.23, 128.41 (2C), 128.58 (2C), 140.20. Found:
C, 76.75; H, 8.31%. Calcd for C14H18O2: C, 77.03; H,
8.51%.
4.5.10. trans-3-Bromo-2-(3-methyl-2-butenoxy)-1-oxa-
cyclohexane (10). IR (neat) 2924, 2872, 2852, 1776,
1676, 1442, 1377, 1204, 1130, 1086, 1072, 1021, 946,
1
869, 727 cmK1; H NMR (CDCl3) d 1.47–1.59 (m, 1H),
1.69 (s, 3H), 1.76 (s, 3H), 1.86–2.00 (m, 2H), 2.34–2.45 (m,
1H), 3.58 (ddd, JZ8.4, 6.3, 5.1 Hz, 1H), 3.88–4.02 (m, 2H),
4.08 (dd, JZ11.7, 6.9 Hz, 1H), 4.22 (dd, JZ11.7, 6.6 Hz,
1H), 4.63 (d, JZ5.1 Hz, 1H), 5.36 (dd, JZ6.9, 6.6 Hz, 1H);
13C NMR (CDCl3) d 17.83, 23.16, 25.67, 29.99, 49.48,
62.36, 64.26, 99.94, 120.11, 138.09. Found: C, 48.28; H,
6.62%. Calcd for C10H17BrO2: C, 48.21; H, 6.88%.
4.5.5. N-(2-Iodoethyl)-N-[(4-methylphenyl)sulfonyl]-2-
propenamine (5a). IR (Nujol) 2856, 1688, 1597, 1454,
1377, 1356, 1335, 1277, 1157, 1109, 1036, 997, 926, 901,
808, 775, 702, 663, 604 cmK1; 1H NMR (CDCl3) d 2.44 (s,
3H), 3.21–3.26 (m, 2H), 3.40–3.45 (m, 2H), 3.80 (d, JZ
6.6 Hz, 2H), 5.16–5.23 (m, 2H), 5.62–5.75 (m, 1H), 7.33 (d,
JZ7.8 Hz, 2H), 7.70 (d, JZ7.8 Hz, 2H); 13C NMR (CDCl3)
d 1.84, 21.40, 50.05, 51.60, 119.69, 127.16 (2C), 129.91
(2C), 132.94, 136.35, 143.76. Found: C, 39.49; H, 4.34; N,
3.70%. Calcd for C12H16O2NSI: C, 39.46; H, 4.42; N,
3.84%.
4.5.11. trans-b-Benzyl-g-nonanolactone (12a). IR (neat)
2928, 2856, 1768, 1604, 1455, 1205, 1173, 999, 944, 751,
1
700 cmK1; H NMR (CDCl3) d 0.87 (t, JZ3.9 Hz, 3H),
1.16–1.58 (m, 8H), 2.29 (dd, JZ7.5, 16.8 Hz, 1H), 2.39–
2.51 (m, 1H), 2.59 (dd, JZ8.1, 16.8 Hz, 1H), 2.68 (dd, JZ
8.1, 14.1 Hz, 1H), 2.83 (dd, JZ6.6, 13.5 Hz, 1H), 4.20 (q,
JZ6.0 Hz, 1H), 7.13–7.35 (m, 5H); 13C NMR (CDCl3) d
13.80, 22.30, 25.05, 31.30, 34.35, 34.73, 39.06, 42.33,
85.29, 126.86, 128.81 (2C), 128.84 (2C), 138.43, 176.46.
Found: C, 77.91; H, 9.19%. Calcd for C16H22O2: C, 78.01;
H, 9.00%.
4.5.6. 3-(2-Bromoethoxy)-1-octene (5b). IR (neat) 2952,
2926, 2856, 1460, 1422, 1321, 1275, 1112, 1083, 994, 927,
1
726 cmK1; H NMR (CDCl3) d 0.89 (t, JZ6.6 Hz, 3H),
1.22–1.68 (m, 8H), 3.45 (t, JZ6.6 Hz, 2H), 3.60 (ddd, JZ
5.7, 6.9, 10.8 Hz, 1H), 3.64–3.71 (m, 1H), 3.81 (dt, JZ10.8,
6.3 Hz, 1H), 5.16–5.23 (m, 2H), 5.62–5.74 (m, 1H); 13C
NMR (CDCl3) d 13.92, 22.48, 24.89, 30.68, 31.63, 35.27,
68.31, 82.01, 117.06, 139.00. Found: C, 50.81; H, 7.96%.
Calcd for C10H19OBr: C, 51.08; H, 8.14%.
4.5.12. trans-b-[(3-Trifluoromethylphenyl)methyl]-g-
nonanolactone (12b). IR (neat) 2930, 2858, 1779, 1452,
1330, 1160, 1118, 1074, 1062, 947, 800, 704, 657 cmK1; 1H
NMR (CDCl3) d 0.87 (t, JZ6.8 Hz, 3H), 1.19–1.60 (m, 8H),
2.29 (dd, JZ7.5, 16.8 Hz, 1H), 2.42–2.54 (m, 1H), 2.61 (dd,
JZ8.3, 16.8 Hz, 1H), 2.76 (dd, JZ8.4, 13.8 Hz, 1H), 2.91
(dd, JZ6.6, 13.8 Hz, 1H), 4.20 (q, JZ6.0 Hz, 1H), 7.35–
7.54 (m, 4H); 13C NMR (CDCl3) d 13.72, 22.25, 25.01,
31.23, 34.32, 34.56, 38.77, 42.09, 85.02, 123.77 (q, JZ
3.7 Hz), 124.01 (q, JZ271.3 Hz), 125.37 (q, JZ3.7 Hz),
4.5.7. 1-[4-(Methylphenyl)sulfonyl]-3-benzylpyrrolidine
(6a). IR (neat) 3022, 2920, 2856, 1599, 1495, 1455, 1345,
1162, 1094, 1032, 816, 743, 701, 662 cmK1 1H NMR
;
(CDCl3) d 1.42–1.54 (m, 1H), 1.81–1.91 (m, 1H), 2.26–2.36
(m, 1H), 2.43 (s, 3H), 2.33 (d, JZ7.5 Hz, 2H), 2.91 (dd, JZ
7.5, 9.9 Hz, 1H), 3.18 (dt, JZ9.9, 7.5 Hz, 1H), 3.31–3.42