Full Paper
À1
À1
1
780, 1457, 1186, 1121, 993, 939, 763, 725, 698 cm ; HRMS (ESI-
1638, 1188, 1125, 1077, 1040, 1003, 945, 840, 750 cm ; HRMS (ESI-
TOF) [M+Na] calcd. 277.0835, found 277.0838.
+
1
+
TOF) [M+Na] calcd. 201.0522, found 201.0517. 3a-trans: H NMR
400 MHz, CDCl ): d=7.44–7.27 (m, 5H), 5.71 (dd, 1H, J=4.2,
.8 Hz), 4.55 (dd, 1H, J=7.7, 7.7 Hz), 2.69 (ddd, 1H, J=7.6, 7.6,
3.2 Hz), 2.61 ppm (ddd, 1H, J=4.2, 7.8, 13.2 Hz); C NMR
125 MHz, CDCl ): d=176.9, 138.8, 128.9, 128.6, 125.0, 78.5, 67.2,
3
(
7
1
3
3 f: According to the general procedure, the desired product 3 f
was obtained in 34% yield (conversion of 2 f=29%, selectivity=
9%, cis/trans=75:25). 3 f-cis: H NMR (400 MHz, CDCl ): d=7.50
(dd, 1H, J=1.6, 7.3 Hz), 7.41–7.27 (m, 3H), 5.74 (dd, 1H, J=5.4,
0.6 Hz), 4.71 (dd, 1H, J=8.4, 11.0 Hz), 3.22 (ddd, 1H, J=5.4, 8.2,
2.7 Hz), 2.07 ppm (ddd, 1H, J=11.0, 11.0, 12.7 Hz); C NMR
125 MHz, CDCl ): d=176.8, 136.0, 131.4, 129.71, 129.67, 127.6,
3
13
1
5
3
(
3
9
2
8.2 ppm; IR (neat): n˜ =3386, 2926, 1775, 1456, 1182, 1122, 1007,
46, 701 cm ; HRMS (ESI-TOF) [M+Na] calcd. 201.0522, found
1
1
À1
+
13
01.0519.
(
1
1
26.2, 74.7, 68.8, 38.4 ppm; IR (neat): n˜ =3394, 2939, 1782, 1576,
3
b: According to the general procedure, the desired product 3b
À1
446, 1322, 1187, 1015, 941, 758, 705 cm ; HRMS (ESI-TOF)
was obtained in 26% yield (conversion of 2b=18%, selectivity=
+
1
1
[M+Na] calcd. 235.0132, found 235.0131. 3 f-trans: H NMR
400 MHz, CDCl ): d=7.41 (m, 1H), 7.32–7.28 (m, 3H), 5.94 (dd, 1H,
7
7
2%, cis/trans=72:28). 3b-cis: H NMR (400 MHz, CDCl ): d=7.95–
.85 (m, 3H), 7.66–7.48 (m, 4H), 6.13 (dd, 1H, J=5.3, 10.8 Hz), 4.82
3
(
3
J=3.6, 8.1 Hz), 4.51 (dd, 1H, J=8.1, 8.1 Hz), 2.78 (ddd, 1H, J=8.2,
(
dd, 1H, J=8.1, 11.0 Hz), 3.23 (ddd, 1H, J=5.2, 8.1, 13.0 Hz),
1
3
1
3
8.2, 13.3 Hz), 2.57 ppm (ddd, 1H, J=3.7, 8.1, 13.2 Hz); C NMR
125 MHz, CDCl ): d=177.0, 136.8, 131.2, 130.1, 129.6, 127.3, 125.1,
2
.39 ppm (ddd, 1H, J=10.9, 10.9, 12.7 Hz); C NMR (125 MHz,
(
7
3
CDCl ): d=176.6, 133.7, 133.3, 130.0, 129.4, 129.2, 126.8, 126.1,
3
6.0, 66.7, 36.9 ppm; IR (neat): n˜ =3420, 2924, 1784, 1474, 1443,
1
2
8
25.5, 122.7, 122.4, 75.1, 69.0, 38.8 ppm; IR (neat): n˜ =3367, 3056,
925, 2855, 1775, 1599, 1510, 1451, 1331, 1199, 1130, 991, 927,
02, 777, 736 cm ; HRMS (ESI-TOF) [M+Na] calcd. 251.0679,
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+
1
123, 1040, 754 cm ; HRMS (ESI-TOF) [M+Na] calcd. 235.0132,
found 235.0131.
g: According to the general procedure, the desired product 3g
was obtained in 32% yield (conversion of 2g=32%, selectivity=
À1
+
1
3
found 251.0674. 3b-trans: H NMR (400 MHz, CDCl ): d=7.94–7.80
3
(
1
m, 3H), 7.62–7.42 (m, 4H), 6.39 (dd, 1H, J=3.3, 8.1 Hz), 4.57 (dd,
H, J=8.2, 8.2 Hz), 2.87 (ddd, 1H, J=8.3, 8.3, 13.0 Hz), 2.75 ppm
1
5
7
1
0%, cis/trans=78:22). 3g-cis: H NMR (400 MHz, CDCl ): d=7.40–
3
1
3
.34 (m, 3H), 7.26 (m, 1H), 5.34 (dd, 1H, J=5.4, 10.9 Hz), 4.68 (dd,
H, J=8.1, 11.1 Hz), 3.02 (ddd, 1H, J=5.4, 8.1, 12.7 Hz), 2.20 ppm
(
ddd, 1H, J=3.4, 8.1, 12.9 Hz); C NMR (125 MHz, CDCl ): d=177.5,
3
1
7
1
34.3, 133.8, 129.4, 129.2, 129.1, 126.8, 126.2, 125.2, 122.4, 121.0,
6.1, 67.0, 37.2 ppm; IR (neat): n˜ =3423, 3057, 2944, 1777, 1600,
512, 1398, 1334, 1261, 1185, 1120, 1001, 942, 790, 734 cm
13
(
ddd, 1H, J=11.1, 11.1, 12.6 Hz); C NMR (125 MHz, CDCl ): d=
3
À1
1
76.3, 139.8, 134.9, 130.2, 129.1, 125.9, 123.8, 76.7, 68.8, 39.5 ppm;
;
+
IR (neat): n˜ =3348, 2925, 1778, 1601, 1435, 1321, 1190, 1128, 997,
HRMS (ESI-TOF) [M+Na] calcd. 251.0679, found 251.0674.
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+
9
2
3
50, 789 cm ; HRMS (ESI-TOF) [M+Na] calcd. 235.0132, found
1
3
c: According to the general procedure, the desired product 3c
35.0129. 3g-trans: H NMR (400 MHz, CDCl ): d=7.36–7.28 (m,
3
was obtained in 30% yield (conversion of 2c=19%, selectivity=
H), 7.18 (m, 1H), 5.67 (dd, 1H, J=4.4, 7.7 Hz), 4.52 (dd, 1H, J=
1
7
7
9%, cis/trans=78:22). 3c-cis: H NMR (400 MHz, CDCl ): d=7.92–
.84 (m, 4H), 7.55–7.50 (m, 2H), 7.45 (dd, 1H, J=1.6, 8.6 Hz), 5.54
3
7.5, 7.5 Hz), 2.71 (m, 1H), 2.56 ppm (ddd, 1H, J=4.4, 7.8, 12.2 Hz);
13
C NMR (125 MHz, CDCl ): d=176.4, 140.9, 135.0, 130.3, 128.7,
3
(
dd, 1H, J=5.2, 10.9 Hz), 4.74 (dd, 1H, J=8.1, 11.2 Hz), 3.07 (ddd,
H, J=5.3, 8.2, 12.8 Hz), 2.34 ppm (ddd, 1H, J=11.2, 11.2, 12.6 Hz);
1
1
25.2, 123.1, 77.6, 67.0, 38.1 ppm; IR (neat): n˜ =3379, 2928, 1776,
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1
672, 1576, 1432, 1181, 1122, 1040, 959, 789 cm ; HRMS (ESI-TOF)
1
3
+
C NMR (125 MHz, CDCl /MeOD): d=177.4, 135.2, 133.3, 132.9,
3
[M+Na] calcd. 235.0132, found 235.0131.
1
28.8, 127.9, 127.6, 126.5, 125.1, 122.9, 77.7, 68.6, 39.6 ppm; IR
3
h: According to the general procedure, the desired product 3h
(
neat): n˜ =3309, 3048, 2998, 1780, 1602, 1445, 1371, 1308, 1205,
was obtained in 31% yield (conversion of 2h=28%, selectivity=
À1
1118, 990, 935, 898, 877, 861, 822, 800, 745 cm ; HRMS (ESI-TOF)
1
5
5%, cis/trans=70:30). 3h-cis: H NMR (400 MHz, CDCl ): d=7.39
3
+
1
[
(
(
M+Na] calcd. 251.0679, found 251.0674. 3c-trans: H NMR
400 MHz, CDCl ): d=7.91–7.82 (m, 3H), 7.76 (brs, 1H), 7.55–7.49
m, 2H), 7.37 (m, 1H), 5.87 (dd, 1H, J=4.4, 7.5 Hz), 4.59 (dd, 1H,
(
d, 2H, J=8.6 Hz), 7.30 (d, 2H, J=8.6 Hz), 5.34 (dd, 1H, J=5.3,
3
1
1
0.9 Hz), 4.68 (dd, 1H, J=8.1, 11.2 Hz), 3.00 (ddd, 1H, J=5.4, 8.2,
2.8 Hz), 2.19 ppm (ddd, 1H, J=11.0, 11.0, 12.6 Hz); C NMR
13
J=7.7, 7.7 Hz), 2.76 (ddd, 1H, J=7.6, 7.6, 13.3 Hz), 2.71 ppm (ddd,
(
125 MHz, CDCl ): d=176.5, 136.3, 135.0, 129.1, 127.2, 76.9, 68.9,
3
1
3
1
1
7
1
H, J=4.4, 7.8, 13.2 Hz); C NMR (125 MHz, CDCl ): d=177.0,
3
3
9.5 ppm; IR (neat): n˜ =3357, 2925, 1777, 1675, 1494, 1320, 1188,
36.1, 133.1, 13.0, 129.0, 128.1, 127.8, 126.8, 126.6, 123.9, 122.6,
À1
+
1128, 1091, 1014, 937, 824, 739 cm ; HRMS (ESI-TOF) [M+Na]
8.6, 67.2, 38.1 ppm; IR (neat): n˜ =3410, 3054, 2929, 1777, 1680,
1
calcd. 235.0132, found 235.0131. 3h-trans: H NMR (400 MHz,
CDCl ): d=7.40–7.35 (m, 2H), 7.26–7.21 (m, 2H), 5.68 (dd, 1H, J=
À1
602, 1508, 1188, 1122, 1075, 1041, 939, 896, 861, 820, 755 cm
;
+
3
HRMS (ESI-TOF) [M+Na] calcd. 251.0678, found 251.0679.
4
1
.5, 7.2 Hz), 4.52 (dd, 1H, J=7.5, 7.5 Hz), 2.69 (ddd, 1H, J=7.3, 7.3,
3.5 Hz), 2.56 ppm (ddd, 1H, J=4.6, 7.6, 13.4 Hz); C NMR
1
3
3
d: According to the general procedure, the desired product 3d
(
125 MHz, CDCl ): d=176.8, 137.3, 134.5, 129.1, 126.5, 78.0, 67.2,
3
was obtained in 31% yield (conversion of 2d=30%, selectivity=
5
7
1
38.2 ppm; IR (neat): n˜ =3402, 2928, 1776, 1493, 1415, 1179, 1123,
2%, cis/trans=75:25). 3d-cis: H NMR (400 MHz, CDCl ): d=7.65–
3
À1
+
1
014, 946, 832, 737, 498 cm ; HRMS (ESI-TOF) [M+Na] calcd.
.56 (m, 4H), 7.45 (t, 4H, J=7.2 Hz), 7.37 (t, 1H, J=7.2 Hz), 5.41
2
35.0132, found 235.0133.
(
dd, 1H, J=5.3, 11.0 Hz), 4.71 (dd, 1H, J=8.1, 11.2 Hz), 3.04 (ddd,
1
H, J=5.2, 8.1, 12.6 Hz), 2.30 ppm (ddd, 1H, J=11.2, 11.2, 12.6 Hz);
3i: According to the general procedure, the desired product 3i
13
C NMR (125 MHz, CDCl /MeOD): d=177.4, 141.8, 140.2, 136.8,
was obtained in 23% yield (conversion of 2i=41%, selectivity=
3
1
1
3
9
28.7, 127.5, 127.4, 127.0, 126.2, 77.2, 68.6, 39.6 ppm; IR (neat): n˜ =
28%, cis/trans=81:19). 3i-cis: H NMR (400 MHz, CDCl ): d=4.52
3
394, 2999, 2961, 2927, 1782, 1637, 1447, 1413, 1198, 1120, 994,
(dd, 1H, J=8.4, 11.1 Hz), 4.32 (m, 1H), 2.70 (ddd, 1H, J=5.0, 8.4,
À1
+
13
38, 841, 766 cm ; HRMS (ESI-TOF) [M+Na] calcd. 277.0835,
11.1 Hz), 1.93–1.67 (m, 3H), 1.02 ppm (t, 3H, J=7.4 Hz); C NMR
1
found 277.0829. 3d-trans: H NMR (400 MHz, CDCl ): d=7.65–7.56
(125 MHz, CDCl ): d=177.2, 78.3, 68.7, 36.6, 28.3, 9.2 ppm; IR
3
3
À1
(
m, 4H), 7.45 (t, 2H, J=7.2 Hz), 7.40–7.34 (m, 3H), 5.76 (dd, 1H, J=
(neat): n˜ =3385, 2971, 1771, 1460, 1203, 1134, 1001, 947, 806 cm
HRMS (ESI-TOF) [M+Na] calcd. 153.0522, found 153.0521. 3i-
trans: H NMR (400 MHz, CDCl ): d=4.58 (m, 1H), 4.50 (dd, 1H, J=
;
+
4
1
.4, 7.6 Hz), 4.58 (dd, 1H, J=7.7, 7.7 Hz), 2.72 (ddd, 1H, J=7.7, 7.7,
13
1
3.3 Hz), 2.65 ppm (ddd, 1H, J=4.4, 7.8, 13.2 Hz); C NMR
3
(
1
125 MHz, CDCl ): d=176.9, 141.6, 140.3, 137.7, 128.9, 127.7, 127.6,
27.1, 125.5, 78.4, 67.3, 38.2 ppm; IR (neat): n˜ =3421, 2923, 1771,
7.7, 7.7 Hz), 2.34 (ddd, 1H, J=7.5, 7.5, 13.3 Hz), 2.27 (ddd, 1H, J=
4.2, 8.2, 12.4 Hz), 1.77–1.61 (m, 2H), 1.01 ppm (t, 3H, J=7.4 Hz);
3
Chem. Asian J. 2016, 11, 1731 – 1737
ꢀ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim