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3q. Isolated as a yellow-viscous oil in 75% yield; 1H NMR (500
MHz, CDCl3) d 7.41–7.34 (m, 2H), 7.22 (td, J ¼ 7.3, 1.1 Hz, 1H),
7.11–7.04 (m, 2H), 4.15 (t, J ¼ 6.5 Hz, 2H), 3.61 (s, 2H), 2.58 (t, J
¼ 7.5 Hz, 2H), 1.80 (p, J ¼ 7.5 Hz, 1H), 1.72 (dq, J ¼ 8.2, 6.6 Hz,
0H), 1.56–1.46 (m, 2H), 1.29 (s, 6H); 13C NMR (126 MHz, CDCl3)
d 175.0, 172.0, 150.7, 129.4, 125.8, 121.5, 64.7, 52.1, 44.6, 34.2,
28.3, 25.5, 24.5, 23.2; HRMS calcd for C17H24ClO4 [M + H]+:
327.1363, found 327.1365.
37.2, 36.6, 34.4, 32.6, 28.0, 26.6, 25.3, 24.8, 22.7, 22.6, 19.6;
HRMS calcd for C19H30O2 [M + H]+: 291.2324, found 291.2326.
3j. Isolated as a colorless oil in 85% yield; 1H NMR (500 MHz,
CDCl3) d 7.42–7.35 (m, 2H), 7.28–7.20 (m, 1H), 7.13–7.05 (m,
2H), 6.85 (s, 3H), 3.95 (t, J ¼ 6.4 Hz, 2H), 3.77 (s, 3H), 2.61 (t, J ¼
7.5 Hz, 2H), 1.84 (ddd, J ¼ 13.7, 8.8, 6.7 Hz, 5H), 1.61 (ddt, J ¼
9.5, 7.0, 2.0 Hz, 2H); 13C NMR (126 MHz, CDCl3) d 172.1, 153.7,
153.1, 150.7, 129.4, 125.7, 121.5, 115.4, 114.6, 68.2, 55.7, 34.2,
29.0, 25.6, 24.6; HRMS calcd for C19H22O4 [M + H]+: 315.1596,
found 315.1597.
3r. Isolated as a colorless oil in 85% yield; 1H NMR (500 MHz,
CDCl3) d 7.38 (t, J ¼ 7.8 Hz, 2H), 7.22 (t, J ¼ 7.4 Hz, 1H), 7.08 (t, J
¼ 6.6 Hz, 2H), 3.69 (s, 3H), 2.64 (ddt, J ¼ 7.1, 4.4, 2.3 Hz, 1H),
2.60–2.54 (m, 1H), 2.50 (p, J ¼ 6.9 Hz, 1H), 1.93–1.86 (m, 1H),
1.84–1.68 (m, 2H), 1.61–1.49 (m, 1H), 1.20 (d, J ¼ 7.0 Hz, 3H);
13C NMR (126 MHz, CDCl3) d 176.8, 171.8, 150.6, 129.4, 125.7,
121.5, 51.6, 39.2, 34.1, 33.0, 24.3, 22.6, 17.1; HRMS calcd for
3k. Isolated as a colorless oil in 79% yield; 1H NMR (500
MHz, CDCl3) d 7.42–7.34 (m, 2H), 7.25–7.20 (m, 3H), 7.11–7.05
(m, 2H), 6.86–6.79 (m, 2H), 3.95 (t, J ¼ 6.4 Hz, 2H), 2.61 (t, J ¼
7.4 Hz, 2H), 1.89–1.79 (m, 4H), 1.66–1.56 (m, 2H); 13C NMR (126
MHz, CDCl3) d 172.0, 157.6, 150.6, 129.4, 129.2, 125.7, 125.3,
121.5, 115.7, 67.8, 34.2, 28.8, 25.5, 24.6.; HRMS calcd for
C
14H19O4 [M + H]+: 251.1283, found 251.1286.
C
18H20ClO3 [M + H]+: 319.1101, found 319.1099.
3s. Isolated as a yellow-viscous oil in 70% yield; 1H NMR (500
3l. Isolated as a colorless oil in 65% yield; 1H NMR (500 MHz,
MHz, CDCl3) d 3.67 (s, 3H), 2.28 (t, J ¼ 7.6 Hz, 2H), 1.64–1.54 (m,
3H), 1.34–1.24 (m, 12H), 1.28–1.19 (m, 6H), 0.88 (td, J ¼ 7.0,
2.3 Hz, 6H); 13C NMR (126 MHz, CDCl3) d 174.3, 51.4, 37.2, 34.5,
33.5, 33.2, 33.1, 31.9, 29.8, 28.9, 26.6, 23.1, 22.7, 22.2, 14.2, 14.1;
HRMS calcd for C16H33O2 [M + H]+: 257.2481, found 257.2492.
3t. Isolated as a red oil in 78% yield; 1H NMR (400 MHz,
CDCl3) d 7.51 (d, J ¼ 7.9 Hz, 2H), 7.36 (s, 1H), 7.31 (t, J ¼ 7.9 Hz,
2H), 7.10 (t, J ¼ 7.4 Hz, 1H), 4.43 (d, J ¼ 5.6 Hz, 2H), 4.35 (d, J ¼
5.6 Hz, 2H), 2.41–2.33 (m, 2H), 1.76–1.64 (m, 4H), 1.30 (s, 3H);
13C NMR (126 MHz, CDCl3) d 170.8, 137.8, 129.0, 124.2, 119.8,
82.7, 39.1, 38.5, 37.7, 23.1, 20.5; HRMS calcd for C14H20NO2 [M +
H]+: 234.1494, found 234.1491.
CDCl3) d 7.41–7.34 (m, 2H), 7.22 (ddt, J ¼ 7.7, 7.0, 1.1 Hz, 1H),
7.11–7.04 (m, 2H), 2.58 (dd, J ¼ 7.9, 7.1 Hz, 2H), 2.23 (tt, J ¼ 7.0,
2.4 Hz, 2H), 2.15 (tt, J ¼ 7.1, 2.4 Hz, 2H), 1.91–1.82 (m, 2H), 1.66–
1.57 (m, 2H), 1.51–1.34 (m, 4H), 0.90 (t, J ¼ 7.2 Hz, 3H); 13C NMR
(126 MHz, CDCl3) d 172.0, 150.7, 129.4, 125.7, 121.5, 80.8, 79.3,
33.9, 31.2, 28.4, 24.1, 21.9, 18.5, 18.4, 13.6; HRMS calcd for
C
17H23O2 [M + H]+: 259.1698, found 259.1696.
3m. Isolated as a colorless oil in 72% yield; 1H NMR (500
MHz, CDCl3) d 7.38 (t, J ¼ 8.0 Hz, 2H), 7.22 (t, J ¼ 7.4 Hz, 1H),
7.07 (d, J ¼ 7.6 Hz, 2H), 2.58 (t, J ¼ 7.5 Hz, 2H), 2.23 (td, J ¼ 6.8,
2.6 Hz, 2H), 1.96 (t, J ¼ 2.6 Hz, 1H), 1.78 (p, J ¼ 7.4 Hz, 2H), 1.65–
1.49 (m, 4H); 13C NMR (126 MHz, CDCl3) d 172.1, 150.7, 129.4,
125.7, 121.6, 84.3, 68.4, 34.2, 28.1, 28.1, 24.4, 18.3; HRMS calcd
for C14H17O2 [M + H]+: 217.1229, found 217.1227.
3u. Isolated as a colorless oil in 80% yield; 1H NMR (500
MHz, CDCl3) d 3.60–3.45 (m, 3H), 3.38 (dq, J ¼ 10.9, 5.0 Hz, 3H),
3.24 (dtd, J ¼ 16.5, 10.0, 7.0 Hz, 1H), 2.96–2.81 (m, 1H), 2.41–
2.26 (m, 2H), 2.23–2.08 (m, 1H), 2.06–1.93 (m, 1H), 1.84–1.60
(m, 5H), 1.60–1.49 (m, 4H), 1.45 (s, 9H); 13C NMR (126 MHz,
CDCl3) d 170.6, 154.6, 79.0, 51.5, 50.9, 46.6, 45.7, 45.4, 42.7, 38.8,
37.9, 31.8, 31.8, 31.0, 29.7, 28.6, 28.5, 26.5, 25.5, 24.5; HRMS
calcd for C17H31N2O3 [M + H]+: 311.2335, found 311.2339.
3v. Isolated as a colorless oil in 75% yield; 1H NMR (500
MHz, CDCl3) d 7.41–7.35 (m, 2H), 7.22 (ddt, J ¼ 7.8, 7.0, 1.1 Hz,
1H), 7.10–7.05 (m, 2H), 4.20 (q, J ¼ 5.9 Hz, 1H), 2.56 (t, J ¼
7.5 Hz, 2H), 2.06–1.98 (m, 1H), 1.84–1.65 (m, 5H), 1.62–1.52 (m,
1H), 1.47–1.31 (m, 5H), 1.17 (dddd, J ¼ 12.8, 8.9, 6.2, 0.8 Hz, 1H),
0.89 (s, 9H), 0.04 (s, 6H); 13C NMR (126 MHz, CDCl3) d 172.3,
150.7, 129.4, 125.7, 121.6, 74.1, 42.6, 37.5, 36.4, 35.3, 34.4, 29.9,
28.0, 25.9, 25.1, 18.1, ꢂ4.7, ꢂ4.7; HRMS calcd for C22H37O3Si [M
+ H]+: 377.2512, found 77.2510.
3n. Isolated as cis-rich stereoisomers (cis/trans ¼ 95 : 5,
1
colorless oil) in 60% yield; H NMR (500 MHz, CDCl3) d 7.41–
7.33 (m, 2H), 7.28–7.15 (m, 1H), 7.11–7.04 (m, 2H), 5.40 (dtt, J ¼
10.8, 6.8, 1.4 Hz, 1H), 5.36 (dtt, J ¼ 10.8, 6.9, 1.4 Hz, 1H), 2.57 (t, J
¼ 7.4 Hz, 2H), 2.16–1.99 (m, 3H), 1.83–1.73 (m, 2H), 1.57 (s, 1H),
1.53–1.43 (m, 2H), 1.38–1.24 (m, 4H), 0.90 (t, J ¼ 7.1 Hz, 3H); 13
C
NMR (126 MHz, CDCl3) d 172.2, 150.7, 130.6, 129.4, 129.0, 125.7,
121.6, 34.3, 31.9, 29.1, 26.9, 26.8, 24.6, 22.3, 14.0; HRMS calcd
for C17H25O2 [M + H]+: 261.1855, found 261.1859.
3o. Isolated as a colorless oil in 78% yield; 1H NMR (500
MHz, CDCl3) d 7.41–7.33 (m, 2H), 7.22 (ddt, J ¼ 7.1, 6.5, 1.1 Hz,
1H), 7.10–7.03 (m, 2H), 4.12 (q, J ¼ 7.1 Hz, 2H), 2.55 (t, J ¼
7.5 Hz, 2H), 2.30 (t, J ¼ 7.5 Hz, 2H), 1.79–1.71 (m, 2H), 1.68–1.57
(m, 2H), 1.47–1.30 (m, 6H), 1.25 (t, J ¼ 7.1 Hz, 3H); 13C NMR (126
MHz, CDCl3) d 173.8, 172.2, 150.7, 129.4, 125.7, 121.5, 60.2,
34.3, 34.3, 28.9, 28.9, 24.9, 24.8, 14.2; HRMS calcd for C17H24O4
[M + H]+: 293.1753, found 293.1755.
3w. Isolated as a cis/trans-mixture (colorless oil) in 75%
1
[66 : 34] yield; H NMR (500 MHz, CDCl3) d 7.43–7.34 (m, 2H),
7.22 (ddd, J ¼ 8.0, 7.0, 1.1 Hz, 1H), 7.08 (ddt, J ¼ 7.6, 2.0, 1.0 Hz,
2H), 3.92 (q, J ¼ 3.5, 3.1 Hz, 0.66H), 3.56–3.46 (m, 0.34H), 2.56
(tdd, J ¼ 7.6, 3.1, 0.9 Hz, 2H), 1.88–1.81 (m, 1H), 1.79–1.68 (m,
3H), 1.66–1.56 (m, 2H), 1.40 (p, J ¼ 4.0, 3.5 Hz, 2H), 1.34–1.19
(m, 4H), 1.22 (s, 1H), 0.90 (d, J ¼ 2.7 Hz, 9H), 0.06 (s, 1H); 13C
NMR (126 MHz, CDCl3) d 172.3, 172.2, 150.8, 129.5, 129.2, 125.8,
125.5, 121.7, 121.4, 72.0, 71.9, 67.4, 67.2, 36.4, 36.0, 34.6, 34.4,
34.4, 34.2, 33.3, 33.2, 31.5, 31.3, 27.1, 26.7, 26.5, 26.0, 26.0, 25.9,
3p. Isolated as a colorless oil in 82% yield; 1H NMR (500
MHz, CDCl3) d 7.37 (dd, J ¼ 8.5, 7.4 Hz, 2H), 7.27–7.18 (m, 1H),
7.08 (dd, J ¼ 8.7, 1.2 Hz, 2H), 3.61 (t, J ¼ 6.6 Hz, 2H), 2.56 (t, J ¼
7.5 Hz, 2H), 1.76 (p, J ¼ 7.5 Hz, 2H), 1.58–1.49 (m, 2H), 1.41–1.31
(m, 6H), 0.90 (s, 9H), 0.06 (s, 6H); 13C NMR (126 MHz, CDCl3)
d 172.3, 150.7, 129.4, 125.7, 121.5, 63.2, 34.4, 32.8, 29.1, 29.0,
26.0, 25.6, 24.9, 18.4, ꢂ5.3.; HRMS calcd for C20H35O3Si [M +
H]+: 351.2355, found 351.2359.
3544 | RSC Adv., 2021, 11, 3539–3546
© 2021 The Author(s). Published by the Royal Society of Chemistry