7844
M. Yoshida et al. / Tetrahedron 58 (2002) 7839–7846
128.6, 128.8, 139.9, 142.5, 149.2, 221.9; MS m/z 276 (Mþ);
Anal. Calcd for C20H20O: C, 86.92; H, 7.29. Found: C,
86.53; H, 7.16.
4.2.7. (2R p,3R p)-2-Methyl-2-[1-(4-nitrophenyl)vinyl]-3-
phenylcyclopentan-1-one (17e). Colorless oil; IR (neat)
1
1740, 1600, 1520, 1340, 860 cm21; H NMR (300 MHz,
CDCl3) d 1.33 (3H, s), 2.23–2.39 (2H, m), 2.50–2.57 (2H,
m), 3.27 (1H, dd, J¼10.8 and 7.5 Hz), 5.09 (1H, s), 5.11
(1H, s), 6.54 (2H, dt, J¼9.0 and 2.1 Hz), 7.18–7.21 (2H, m),
7.31–7.33 (3H, m), 7.88 (2H, dt, J¼9.0 and 2.1 Hz); 13C
NMR (75 MHz, CDCl3) d 24.2, 24.3, 37.6, 54.7, 58.4,
120.4, 122.6, 127.5, 128.5, 128.6, 129.4, 139.5, 146.7,
148.2, 149.0, 220.9; MS m/z 321 (Mþ); HRMS calcd for
C20H19NO3 (Mþ) 321.1364, found 321.1342.
4.2.2. [(2R p,3R p) and (2R p,3R p)]-2-Methyl-2-(1-phenyl-
vinyl)-3-phenylcyclopentan-1-ones (17a118a) (ratio of
1
60:40). Colorless oil; H NMR (300 MHz, CDCl3) d 0.95
(3H£0.4, s), 1.36 (3H£0.6, s), 2.10–2.45 (3H and 1H£0.6,
m), 2.61–2.70 (1H£0.4, m), 3.22 (1H£0.6, t, J¼9.0 Hz),
3.58 (1H£0.4, dd, J¼11.4 and 6.9 Hz), 4.87 (1H£0.6, s),
5.01 (1H£0.6, s), 5.22 (1H£0.4, s), 5.34 (1H£0.4, s), 6.54
(2H, dt, J¼6.9 and 1.5 Hz), 7.04–7.13 (3H, m), 7.22–7.24
(2H, m), 7.30–7.33 (3H, m).
4.2.8. (2R p,3R p)-2-(4-Acetylphenylvinyl)-2-methyl-3-
phenylcyclopentanone (17f). Colorless oil; IR (neat)
1
4.2.3. (2R p,3R p)-2-Methyl-2-[1-(4-methoxyphenyl)vinyl]-
3-phenylcyclopentan-1-one (17b). Colorless oil; IR (neat)
1730, 1600 cm21; 1H NMR (500 MHz, CDCl3) d 1.33 (3H,
s), 2.11–2.17 (2H, m), 2.38–2.42 (2H, m), 3.18 (1H, dd,
J¼11.5 and 7.5 Hz), 3.72 (3H, s), 4.80 (1H, d, J¼0.5 Hz),
4.96 (1H, d, J¼0.5 Hz), 6.44 (2H, dt, J¼5.4 and 1.5 Hz),
6.58 (2H, dt, J¼5.4 and 1.2 Hz), 7.20–7.24 (2H, m), 7.27–
7.32 (3H, m); 13C NMR (75 MHz, CDCl3) d 24.2, 24.3,
37.8, 55.0, 55.1, 59.0, 112.9, 118.6, 127.1, 128.3, 128.9,
129.9, 135.0, 140.0, 148.8, 158.7, 222.3; MS m/z 306 (Mþ);
HRMS calcd for C21H22O2 (Mþ) 306.1619, found
306.1601.
1736, 1682, 1604 cm21; H NMR (300 MHz, CDCl3) d
1.34 (3H, s), 2.21 (1H, dd, J¼8.7 and 7.5 Hz), 2.22 (1H, dd,
J¼8.7 and 7.5 Hz), 2.45–2.51 (2H, m), 2.53 (3H, s), 3.24
(1H, dd, J¼7.4 and 7.4 Hz), 4.98 (1H, s), 5.06 (1H, s), 6.56
(2H, dt, J¼9.0 and 1.8 Hz), 7.19–7.24 (2H, m), 7.30–7.36
(3H, m), 7.63 (2H, J¼9.0 and 1.8 Hz); 13C NMR (75 MHz,
CDCl3) d 24.1, 24.3, 26.4, 37.6, 54.8, 58.6, 119.6, 127.3,
127.5, 128.4, 128.7, 128.8, 135.6, 139.7, 147.4, 148.8,
198.0, 221.4; MS m/z 318 (Mþ); HRMS calcd for C22H22O2
(Mþ) 318.1620, found 318.1642.
4.2.9. (2R p,3R p)-2-Methyl-2-[3,4-(methylenedioxy)phenyl]-
vinyl-3-phenylcyclopentan-1-one (17h). IR (neat) 1734,
1
4.2.4. (2R p,3R p)-2-Methyl-2-[1-(4-methylphenyl)vinyl]-
3-phenylcyclopentan-1-one (17c). Colorless oil; IR (neat)
1738, 1603 cm21; 1H NMR (300 MHz, CDCl3) d 1.34 (3H,
s), 2.12–2.18 (2H, m), 2.25 (3H, s), 2.39–2.44 (2H, m),
3.20 (1H, dd, J¼11.1 and 7.8 Hz), 4.82 (1H, s), 5.00 (1H, s),
6.43 (2H, dt, J¼6.3 and 3.3 Hz), 6.81 (2H, d, J¼7.5 Hz),
7.22–7.26 (2H, m), 7.28–7.36 (2H, m); 13C NMR (75 MHz,
CDCl3) d 20.9, 24.1, 24.2, 37.7, 55.0, 58.9, 118.6, 127.0,
128.1, 128.2, 128.5, 128.8, 136.6, 139.6, 139.9, 149.1,
222.1; MS m/z 290 (Mþ); HRMS calcd for C21H22O (Mþ)
290.1671, found 290.1659.
1600 cm21; H NMR (400 MHz, CDCl3) d 1.32 (3H, s),
2.12–2.27 (2H, m), 2.42–2.52 (2H, m), 3.21 (1H, dd,
J¼12.0 and 6.8 Hz), 4.82 (1H, s), 4.99 (1H, s), 5.81–5.88
(3H, m), 6.08 (1H, dd, J¼8.1 and 1.7 Hz), 6.51 (1H, d,
J¼7.8 Hz), 7.13–7.40 (5H, m); 13C NMR (75 MHz, CDCl3)
d 24.0, 24.3, 37.7, 54.8, 54.9, 58.9, 100.8, 107.3, 109.0,
118.8, 122.1, 122.3, 128.1, 128.6, 128.9, 136.3, 139.9,
148.8, 221.9; MS m/z320 (Mþ); Anal. Calcd for C21H20O3:
C, 78.73; H, 6.29. Found: C, 78.42; H, 6.34.
4.2.10. [(2R p,3R p) and (2S p,3R p)]-2-Methyl-2-[3,4-
(methylenedioxy)phenyl]vinyl-3-phenylcyclopentan-1-
ones (17h118h) (ratio of 84:16). IR (neat) 1730,
4.2.5. [(2R p,3R p) and (2S p,3R p)]-2-Methyl-2-[1-(4-methyl-
phenyl)vinyl]-3-phenylcyclopentan-1-ones (17c118c)
(ratio of 94:6). Colorless oil; 1H NMR (300 MHz, CDCl3) d
0.94 (3H£0.06, s), 1.34 (3H£0.94, s), 2.12–2.22 (2H, m), 2.25
(3H£0.94, s), 2.35 (3H£0.06, s), 2.39–2.44 (2H, m), 3.20 (1H,
dd, J¼11.1 and 7.8 Hz), 4.82 (1H£0.94, d, J¼0.6 Hz), 5.00
(1H£0.94, d, J¼0.6 Hz), 6.43 (2H£0.94, dt, J¼6.3 and
3.3 Hz), 6.54 (2H£0.06, d, J¼6.3 Hz), 6.81 (2H, d, J¼
7.5 Hz), 7.02–7.08 (2H£0.06, m), 7.11–7.17 (3H£0.06, m),
7.22–7.26 (2H£0.94, m), 7.28–7.36 (3H£0.94, m).
1600 cm21
;
1H NMR (400 MHz, CDCl3) d 0.93 (3H£
0.16, s), 1.32 (3H£0.84, s), 2.12–2.27 (2H, m), 2.42–2.52
(2H, m), 3.21 (1H£0.84, dd, J¼12.0 and 6.8 Hz), 3.61
(1H£0.16, dd, J¼11.2 and 7.3 Hz), 4.82 (1H£0.84, s), 4.99
(1H£0.84, s), 5.15 (1H£0.16, s), 5.30 (1H£0.16, s), 5.81–
5.88 (3H, m), 5.93 (1H£0.16, s), 6.08 (1H£0.84, dd, J¼8.1
and 1.7 Hz), 6.51 (1H£0.84, d, J¼8.1 and 1.7 Hz), 6.68 (1H£
0.16, m), 7.13–7.40 (5H, m); MS m/z 320 (Mþ); HRMS
calcd for C21H20O3 (Mþ) 320.1412, found 320.1418.
4.2.6. [(2R p,3R p) and (2S p,3R p)]-2-Methyl-2-[1-(1-
naphthyl)vinyl]-3-phenylcyclopentan-1-ones (17d118d)
4.2.11. (2R p,3R p)-2-Methyl-2-(1-methylene-2-phenyl-2-
propenyl)-3-phenylcyclopentan-1-one (17i). IR (neat)
;
1732, 1602 cm21 1H NMR (300 MHz, CDCl3) d 1.24
(ratio of 84:16). Colorless oil; IR (neat) 1740, 1620 cm21
;
1H NMR (500 MHz, CDCl3) d 1.01 (3H£0.84, s), 1.50
(3H£0.16, s), 2.10–2.24 (1H£0.16, m), 2.27–2.32 (1H£
0.84, m), 2.41–2.50 (3H£0.16, m), 2.53–2.74 (3H£0.84,
m), 3.27 (1H, m), 4.99 (1H£0.16, s), 5.06 (1H£0.16, s), 5.11
(1H£0.84, s), 5.22 (1H, d, J¼7.3 Hz), 5.27 (1H£0.84, s),
6.92 (1H£0.84, t, J¼7.3 Hz), 7.08 (1H£0.16, d, J¼
14.0 Hz), 7.25–7.47 (7H and 2H£0.16, m), 7.56 (1H£
0.84, d, J¼5.1 Hz), 7.70–7.72 (1H, m), 8.07 (1H£0.84, d,
(3H, s), 2.15–2.45 (4H, m), 3.14 (1H, dd, J¼10.4 and
5.8 Hz), 4.16 (1H, s), 4.86 (1H, s), 5.03 (1H, s), 5.07 (1H, s),
7.20–7.36 (10H, m); 13C NMR (75 MHz, CDCl3) d 24.4,
37.4, 55.5, 58.3, 115.9, 116.0, 120.1, 127.3, 128.0, 128.4,
129.2, 140.1, 140.7, 148.5, 151.0, 221.0; MS m/z302 (Mþ);
HRMS calcd for C22H22O 302.1671, found 302.1651.
4.2.12. (2R p,3S p)-2-[1-(4-Methoxyphenyl)vinyl]-2-phenyl-
3-phenylcyclopentan-1-one (19) (entry 1 in Table 3).
;
Colorless oil; IR (neat) 1730, 1600 cm21 1H NMR
1
J¼5.1 Hz); MS m/z 326 (Mþ); HRMS calcd for C24H22O
(Mþ) 326.1671, found 326.1686.