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filtered, and concentrated. The organic phase was dried (MgSO4) and concentrated in vacuo to give
a brown oil, which was subjected to column chromatography over silica gel (hexane/EtOAc = 20/1,
v/v) to give 2a (234 mg, 74%, Rf = 0.51; hexane/EtOAc = 4/1, v/v).
Dimethyl 2-[(2E,5E)-5-benzylidenehept-2-enyl]malonate (2a): IR (neat) 3022 (w), 2962 (s), 2875
1
(w), 1736 (s), 1647 (w), 1599 (w), 1435 (s), 1197 (s), 1153 (s), 1028 (m), 920 (w), 700 (s) cm-1; H
NMR (CDCl3, 400 MHz) ! 1.05 (t, J = 7.6 Hz, 3 H), 2.21 (q, J = 7.6 Hz, 2 H), 2.65 (t, J = 7.0 Hz, 2
H), 2.84 (d, J = 6.8 Hz, 2 H), 3.46 (t, J = 7.0 Hz, 1 H), 3.72 (s, 6 H), 5.48 (dt, J = 15.4, 6.8 Hz, 1 H),
13
5.60 (dt, J = 15.4, 7.0 Hz, 1 H), 6.20 (s, 1 H), 7.15-7.31 (m, 5 H); C NMR (CDCl3, 100 MHz) !
12.8, 23.8, 31.8, 39.7, 51.8, 52.3, 125.1, 125.7, 126.9, 127.7, 128.2, 131.3, 138.0, 142.9, 168.9.
High-resolution MS, calcd for C19H24O4: 316.1675. Found m/z (relative intensity): 316.1678 (M+,
100), 317 (24), 285 (11).
1-[(1E,4E)-2-Ethyldeca-1,4,9-trienyl]benzene (3a): IR (neat) 3022 (w), 2966 (s), 2930 (s), 2856 (s),
1641 (m), 1599 (m), 1493 (s), 1443 (m), 970 (s), 912 (s), 698 (s) cm-1; 1H NMR (CDCl3, 400 MHz) !
1.07 (t, J = 7.6 Hz, 3 H), 1.49 (quint, J = 7.4 Hz, 2 H), 2.04–2.09 (m, 4 H), 2.25 (q, J = 7.6 Hz, 2 H),
2.85 (d, J = 5.5 Hz, 2 H), 4.94 (d, J = 10.2 Hz, 1 H), 5.00 (d, J = 17.1 Hz, 1 H), 5.42–5.56 (m, 2 H),
13
5.81 (ddt, J = 17.1, 10.2, 6.7 Hz, 1 H), 6.24 (s, 1 H), 7.12-7.31 (m, 5 H); C NMR (CDCl3, 100
MHz) ! 12.9, 23.8, 28.8, 32.0, 33.2, 40.1, 114.3, 124.9, 125.8, 127.9, 128.1, 132.0, 138.4, 143.8.
High-resolution MS, calcd for C18H24: 240.1878, Found m/z (relative intensity): 240.1867 (M+, 100),
211 (73), 241 (45).
(3R*,4R*)-3-Allyl-4-[(1E,4E)-4-ethyl-7-(tetrahydro-2H-pyran-2-yloxy)hepta-1,4-dienyl]-1-tosyl-
pyrrolidine (4g): IR (neat) 3076 (w), 2939 (s), 2872 (s), 2359 (s), 2341 (s), 1641 (s), 1599 (s), 1441
(m), 1346 (s), 1163 (s), 1032 (s), 814 (m), 667 (s) cm-1; 1H NMR (CDCl3, 400 MHz) ! 0.93 (t, J = 7.6
Hz, 3 H), 1.49-1.57 (m, 6 H), 1.79-1.85 (m, 2 H), 1.99 (q, J = 7.6 Hz, 2 H), 2.22 (br dd, J = 9.6, 6.5
Hz, 1 H), 2.24 (t, J = 8.5 Hz, 1 H), 2.30 (q, J = 7.1 Hz, 2 H), 2.44 (s, 3 H), 2.67 (d, J = 6.8 Hz, 2 H),
2.88 (dd, J = 9.8, 8.5 Hz, 1 H), 2.94 (t, J = 9.8 Hz, 1 H), 3.36 (t, J = 9.6 Hz, 2 H), 3.47-3.51 (m, 2 H),
3.68 (dt, J = 16.8, 7.3 Hz, 1 H), 3.85 (td, J = 15.1, 7.3 Hz, 1 H), 4.58 (t, J = 6.8 Hz, 1 H), 4.95 (d, J =
10.5 Hz, 1 H), 4.98 (d, J = 17.1 Hz, 1 H), 5.09 (dd, J = 15.2, 8.5 Hz, 1 H), 5.13 (t, J = 7.1 Hz, 1 H),
5.40 (dt, J = 15.2, 6.8 Hz, 1 H), 5.62 (ddd, J = 17.1, 10.5, 7.8 Hz, 1 H), 7.31 (d, J = 8.2 Hz, 2 H), 7.70
13
(d, J = 8.2 Hz, 2 H); C NMR (CDCl3, 100 MHz) ! 13.0, 19.6, 21.5, 23.2, 25.5, 28.4, 30.7, 35.5,
39.7, 44.0, 47.5, 52.6, 53.0, 62.3, 67.2, 98.7, 116.5, 121.0, 127.4, 129.5, 131.9, 134.1, 135.4, 141.2,
143.1. High-resolution MS, calcd for C28H41NO4S: 487.2756. Found m/z (relative intensity):
487.2759 (M+, 100).
8. Palladium Reagents and Catalysts; ed. by J. Tsuji; John-Wiley & Sons, Chichester, 1995; M.
Takacs, Palladium-Catalyzed Oligomerization and Polymerization of Dienes and Related