Y. Kobayashi et al. / Tetrahedron Letters 53 (2012) 3742–3745
3745
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19. Reaction of 1c with phenyl vinyl ketone under the conditions for 2a gave the
product only in 10%.
20. The 1H and/or 13C NMR spectra of 5A, 5B, 5C, and 5D were identical with those
reported. 5A: Refs. 5a,c,6l 5B: Refs. 5a,c,6i 5C: Refs. 4c,5a,c,6i,l 5D: Ref. 6s The
NMR spectra of the intermediates are as follows: Compound 6c: 1H NMR
(300 MHz, CDCl3) d 1.34 (s, 9H), 2.14 (s, 3H), 2.80 (t, J = 7 Hz, 2H), 3.63 (dt,
J = 14, 7 Hz, 1H), 3.99 (dt, J = 14, 7 Hz, 1H), 6.98 (t, J = 8 Hz, 1H), 7.15 (d, J = 8 Hz,
1H), 7.34 (t, J = 8 Hz, 1H), 7.85 (d, J = 8 Hz, 1H); 13C NMR (75 MHz, CDCl3) d
28.0, 29.8, 42.1, 44.5, 80.1, 100.2, 128.5, 128.8, 129.3, 139.2, 144.3, 153.5, 206.5.
Compound 3c: 1H NMR (300 MHz, CDCl3) d 1.53 (s, 9H), 1.58 (s, 3H), 1.82 (s,
1H), 2.02 (t, J = 6 Hz, 1H), 3.65 (dt, J = 13, 6 Hz, 1H), 3.94 (dt, J = 13, 6 Hz, 1H),
7.09 (t, J = 8 Hz, 1H), 7.22 (t, J = 8 Hz, 1H), 7.54 (d, J = 8 Hz, 1H), 7.70 (d, J = 8 Hz,
1H); 13C NMR (75 MHz, CDCl3) d 28.3, 29.3, 39.1, 41.6, 68.7, 81.0, 123.6, 123.8,
125.5, 127.2, 134.9, 136.9, 153.5. Compound 6d: 1H NMR (300 MHz, CDCl3) d
1.35 (s, 9H), 2.15 (s, 3H), 2.31 (s, 3H), 2.79 (t, J = 7 Hz, 2H), 3.62 (dt, J = 14, 7 Hz,
1H), 3.97 (dt, J = 14, 7 Hz, 1H), 7.01 (d, J = 7 Hz, 1H), 7.13 (d, J = 7 Hz, 1H), 7.68
(s, 1H); 13C NMR (75 MHz, CDCl3) d 20.3, 28.0, 29.8, 42.1, 44.6, 80.0, 99.9, 128.8,
129.6, 138.6, 139.6, 141.7, 153.7, 206.7. Compound 3d: 1H NMR (300 MHz,
CDCl3) d 1.52 (s, 9H), 1.58 (s, 3H), 2.01 (t, J = 6 Hz, 2H), 2.32 (s, 3 H), 3.57–3.68
(m, 1H), 3.88–3.98 (m, 1H), 7.03 (d, J = 8 Hz, 1H), 7.34 (s, 1H), 7.57 (d, J = 8 Hz,
1H); 13C NMR (75 MHz, CDCl3) d 20.9, 28.4, 29.5, 39.3, 41.7, 68.9, 81.0, 123.8,
125.9, 128.1, 133.1, 134.4, 134.6, 153.6. Compound 6e: 1H NMR (300 MHz,
CDCl3) d 1.34 (s, 9H), 2.15 (s, 3H), 2.78 (t, J = 7 Hz, 1H), 3.58 (dt, J = 14, 7 Hz, 1H),
3.79 (s, 3H), 3.98 (dt, J = 14, 7 Hz, 1H), 6.86 (dd, J = 8, 3 Hz , 1H), 7.03 (d, J = 8 Hz,
1H), 7.35 (d, J = 3 Hz, 1H); 13C NMR (75 MHz, CDCl3) d 28.2, 30.1, 42.4, 44.9,
55.6, 80.3, 100.5, 114.6, 124.2, 129.5, 137.4, 154.2, 158.5, 207.2. Compound 3e:
1H NMR (300 MHz, CDCl3) d 1.52 (s, 9H), 1.56 (s, 3H), 1.87 (s, 1H), 1.97–2.05 (m,
2H), 3.57–3.68 (m, 1H), 3.80 (s, 3H), 3.85–3.96 (m, 1H), 6.79 (dd, J = 9, 3 Hz,
1H), 7.06 (d, J = 3 Hz, 1H), 7.59 (d, J = 9 Hz, 1H); 13C NMR (75 MHz, CDCl3) d
28.4, 29.4, 39.4, 41.7, 55.5, 69.2, 80.9, 110.2, 113.4, 125.3, 130.3, 136.3, 153.8,
155.9. Compound 6f: 1H NMR (300 MHz, CDCl3) d 1.35 (s, 9H), 2.16 (s, 3H), 2.80
(t, J = 7 Hz, 2H), 3.59 (dt, J = 14, 7 Hz, 1H), 3.98 (dt, J = 14, 7 Hz, 1H), 6.99–7.20
(m, 2H), 7.56 (dd, J = 8, 3 Hz, 1H); 13C NMR (75 MHz, CDCl3) d 28.3, 30.0, 42.2,
44.7, 80.5, 100.0 (d, J = 9 Hz), 115.9 (d, J = 22 Hz), 126.0 (d, J = 24 Hz), 130.0 (d,
J = 9 Hz), 140.9 (d, J = 3 Hz), 153.7, 160.4 (d, J = 250 Hz), 206.8. Compound 3f:
1H NMR (300 MHz, CDCl3) d 1.52 (s, 9H), 1.55 (s, 3H), 1.80 (s, 1H), 2.01 (ddd,
J = 7, 5, 3.5 Hz, 2H), 3.64 (ddd, J = 13, 7, 5 Hz, 1H), 3.91 (ddd, J = 13, 7, 5 Hz, 1H),
6.92 (dd, J = 9, 8, 3 Hz, 1H), 7.23 (dd, J = 9, 3 Hz, 1H), 7.67 (dd, J = 9, 5 Hz, 1H);
13C NMR (75 MHz, CDCl3) d 28.3, 29.2, 39.0, 41.7, 68.9, 81.3, 111.9 (d, J = 23 Hz),
114.2 (d, J = 22 Hz), 125.6 (d, J = 8 Hz), 132.9 (d, J = 3 Hz), 137.1 (d, J = 7 Hz),
155.5 (d, J = 285 Hz), 160.7. Compound 6g: 1H NMR (300 MHz, CDCl3) d 1.34 (s,
9 H), 2.41 (quint., J = 8 Hz, 1H), 2.59 (t, J = 8 Hz, 1H), 2.75 (t, J = 8 Hz, 1H), 3.63
(dt, J = 14, 7 Hz, 1H), 3.97 (dt, J = 14, 7 Hz, 1H), 6.98 (t, J = 8 Hz, 1H), 7.11–7.37
(m, 7H), 7.85 (d, J = 9 Hz, 1H). Compound 3g: 1H NMR (300 MHz, CDCl3) d 1.51
(s, 9H), 1.44–1.96 (m, 5H), 2.10 (ddd, J = 14, 8, 4 Hz, 1H), 2.48–2.69 (m, 2H),
3.46 (ddd, J = 13, 7, 5 Hz, 1H), 4.00 (ddd, J = 13, 7, 5 Hz, 1H), 7.03–7.31 (m, 7H),
7.44 (d, J = 8 Hz, 1H), 7.68 (d, J = 8 Hz, 1H); 13C NMR (75 MHz, CDCl3) d 25.7,
28.4, 36.0, 36.6, 40.5, 41.4, 70.9, 81.1, 123.7, 124.0, 125.3, 125.8, 127.2, 128.3,
128.4, 134.7, 137.3, 142.1, 153.6. Compound 5E: 1H NMR (300 MHz, CDCl3) d
2.11 (quint., J = 8 Hz, 2H), 2.77 (t, J = 8 Hz, 2H), 3.10 (t, J = 8 Hz, 2H), 7.18–7.35
(m, 6H), 7.53 (t, J = 7 Hz, 1H), 7.70 (t, J = 7 Hz, 1H), 7.95 (d, J = 9 Hz, 1H), 8.11 (d,
J = 9 Hz, 1H), 8.81 (d, J = 4 Hz, 1H); 13C NMR (75 MHz, CDCl3) d 31.5, 35.7, 120.8,
123.5, 126.0, 126.3, 127.5, 128.5, 129.0, 130.2, 141.5, 148.2, 148.3, 150.2.
Compound 6h: 1H NMR (400 MHz, CDCl3) d 1.1–1.4 (m, 6H), 1.34 (s, 9H), 1.62–
1.86 (m, 4H), 2.27–2.38 (m, 1H), 2.26–2.42 (m, 2H), 3.65 (ddd, J = 15, 9, 6 Hz,
1H), 3.93 (ddd, J = 15, 8, 6.5 Hz, 1H), 6.98 (t, J = 8 Hz, 1H), 7.11–7.23 (m, 1H),
7.33 (d, J = 8 Hz, 1H), 7.85 (d, J = 8 Hz, 1H). Compound 3h: 1H NMR (400 MHz,
CDCl3) d 0.86–0.98 (m, 1H), 1.03–1.36 (m, 5H), 1.51 (s, 9H), 1.61–1.96 (m, 6H),
2.16 (ddd, J = 14, 10, 5 Hz, 1H), 3.25 (ddd, J = 13, 10, 4 Hz, 1H), 4.12 (dt, J = 5,
13 Hz, 1H), 7.09 (t, J = 8 Hz, 1H), 7.19 (t, J = 8 Hz, 1H), 7.45 (d, J = 8 Hz, 1H), 7.60
(d, J = 8 Hz, 1H); 13C NMR (100 MHz, CDCl3) d 26.5 (m), 27.7, 28.4, 33.7, 41.2,
46.8, 73.3, 80.9, 123.9, 124.4, 125.5, 127.0, 135.0, 138.0, 153.6. Compound 5F:
1H NMR (400 MHz, CDCl3) d 1.28–1.44 (m, 1H), 1.47–1.63 (m, 4H), 1.82–2.08
(m, 5H), 3.27–3.41 (m, 1H), 7.28 (d, J = 4.5 Hz, 1H), 7.56 (t, J = 8 Hz, 1H), 7.69 (t,
J = 8 Hz, 1H), 8.10 (d, J = 8 Hz, 1H), 8.13 (d, J = 8 Hz, 1H), 8.84 (d, J = 4.5 Hz, 1H);
13C NMR (100 MHz, CDCl3) d 26.3, 27.0, 33.6, 39.0, 117.5, 123.1, 126.3, 127.0,
128.9, 130.3, 148.2, 150.3, 153.7.
12. Igarashi, J.; Kobayashi, Y. Tetrahedron Lett. 2005, 46, 6381–6384.