European Journal of Organic Chemistry
10.1002/ejoc.201601549
FULL PAPER
1
=
=
5
1
1
7
H), 3.82 (s, 3H), 3.56 (dd, J = 10.9, 7.2 Hz, 1H), 3.21 (m, 1H), 2.72 (dd, J
8.4, 5.0, 2H), 1.32 (d, J = 7.1 Hz, 3H), 1.22 (t, J = 7.2 Hz, 3H), 1.03 (t, J
Diethyl
2-hydroxy-4-(4-methoxyphenyl)-3-methyl-3-(naphthalen-2-
yl)cyclopentane-1,1-dicarboxylate: Reaction time: 7 h, 1a (100 mg, 0.34
mmol), 2d (75 mg, 0.41 mmol),
7.2 Hz, 3H). 13C-NMR (100 MHz, CDCl
5.4, 61.7, 61.9, 63.7, 78.8, 85.4, 113.9, 126.3, 127.7, 128.2, 128.3, 132.8,
3
): δ 13.8, 14.1, 19.6, 41.8, 43.6,
-
1
44.9, 159.4, 169.3, 171.0. IR (CHCl
762, 1662, 1524, 1454, 1340, 1241, 1165, 1088, 1037, 862, 831, 798,
46, 702. HRMS (ESI) m/z: [M+Na]+ calcd. for C25
Na 449.1935;
3
): max (cm ) 3019, 2954, 2942, 2886,
(3h, trans): viscous liquid, 65 mg, yield: 40%,
R
f
value: 0.34
1
(EtOAc/Hexane) =1:10, (v/v). H-NMR (400 MHz, CDCl
3
): δ 7.72 – 7.63 (m,
30 6
H O
3
1
1
H), 7.48 (d, J = 8.7 Hz, 1H), 7.38 – 7.35 (m, 2H), 7.01 – 6.98 (d, J = 8.7,
H), 6.77 (d, J = 8.7 Hz, 2H), 6.51 (d, J = 8.7 Hz, 2H), 5.52 (d, J = 8.2 Hz,
H), 4.35 (q, J = 7.2 Hz, 2H), 4.28 (q, J = 7.2 Hz, 2H), 3.91 (d, J = 8.2 Hz,
found 449.1921.
5
(
f (trans, minor): 1H-NMR (400 MHz, CDCl
d, J = 7.2 Hz, 2H), 7.15 (m, 1H), 6.78 (d, J = 7.2 Hz, 2H), 5.24 (t, J = 7.5
Hz, 1H), 5.08 (d, J = 8.1 Hz, 1H), 3.96 (m, 2H), 3.94 (m, 1H), 3.79 (s, 3H),
.49 (dd, J = 10.8, 7.2 Hz, 1H), 3.28 (t, J = 7.5 Hz, 1H), 3.19 (m, 1H), 2.35
dd, J = 13.6, 7.4 Hz, 1H), 1.31 (d, J = 6.9 Hz, 3H), 1.09 (t, J = 7.2 Hz, 3H),
3
): δ 7.33-7.29 (m, 4H), 2.25
1H), 3.62 (s, 3H), 3.52 (dd, J = 10.2, 7.5 Hz, 1H), 2.96 (dd, J = 14.2, 7.5
Hz, 1H), 2.45 (dd, J = 14.2, 10.2 Hz, 1H), 1.35 (t, J = 7.2 Hz, 3H), 1.33 –
1.27 (m, 6H). 13C-NMR (100 MHz, CDCl
3
): δ 14.2, 24.6, 37.7, 53.1, 53.9,
3
55.2, 62.2, 62.3, 62.5, 83.1, 113.2, 125.4, 125.5, 125.6, 126.8, 126.9,
(
127.3, 128.2, 129.6, 131.5, 133.0, 133.5, 143.0, 157.8, 171.7, 171.8. IR
.05 (m, 3H). 13C-NMR (100 MHz, CDCl
5.4, 61.5, 61.9, 63.7, 78.4, 86.1, 113.9, 126.4, 126.9, 128.2, 128.3, 134.7,
44.7, 159.1, 169.0, 170.4.
(CHCl
): max (cm ) 3510 (broad OH), 3058, 2932, 2876, 1727, 1696, 1513,
-1
1
5
1
3
): δ 13.8, 13.9, 20.0, 40.5, 43.6,
3
1466, 1381, 1251, 1181, 1097, 1037, 858, 832, 812, 745, 703. HRMS (ESI)
+
m/z: [M+Na] calcd. for C29
32 6
H O Na 499.2091; found 499.2069.
(
2R,4S)-diethyl
2-hydroxy-4-(4-methoxyphenyl)-3-methyl-3-
(4h, cis): viscous liquid, 16 mg, Yield: 10%,
(EtOAc/Hexane) =1:10, (v/v). H -NMR (400 MHz, CDCl
R
f
value: 0.31
1
(naphthalen-1-yl)cyclo-pentane-1,1-dicarboxylate (4g): Reaction time:
3
): δ 7.84 – 7.78
2
h, 1a (100 mg, 0.34 mmol), 2c (75 mg, 0.41 mmol), viscous liquid, 89
(m, 2H), 7.74 (m, 1H), 7.64 (s, 1H), 7.56 (m, 1H), 7.45 – 7.42 (m, 2H), 6.78
(d, J = 8.8 Hz, 2H), 6.64 (d, J = 8.8 Hz, 2H), 5.34 (d, J = 7.1 Hz, 1H), 4.34
– 4.27 (m, 4H), 3.71 (s, 3H), 3.54 (dd, J = 13.6, 6.8 Hz, 1H), 3.33 (d, J =
7.1 Hz, 1H), 3.18 (t, J = 13.6 Hz, 1H), 2.62 (dd, J = 13.6, 6.8 Hz, 1H), 1.32
1
mg, yield: 55%, R
MHz, CDCl
J = 7.1 Hz, 1H), 7.46 – 7.34 (m, 3H), 7.29 (s, 1H), 6.61 (d, J = 8.7 Hz, 2H),
.55 (d, J = 8.7 Hz, 2H), 5.99 (s, 1H), 4.41 (dd, J = 13.4, 7.2Hz, 1H), 4.24
m, 5H), 3.62 (s, 3H), 3.22 (t, J = 13.4 Hz, 1H), 2.66 (dd, J = 13.4, 7.2 Hz,
f
value: 0.32 (EtOAc/Hexane) =1:10, (v/v), H -NMR (400
3
): δ 8.39 (d, J = 8.2 Hz, 1H), 7.85 (d, J = 7.7 Hz, 1H), 7.69 (d,
6
(m, 9H). 13C-NMR (100 MHz, CDCl
3
): δ 12.7, 14.2, 14.3, 36.5, 50.1, 53.9,
(
55.3, 60.6, 62.1, 62.2, 84.8, 113.3, 125.0, 125.8, 126.0, 126.1, 127.4,
127.9, 128.4, 129.5, 130.1, 132.2, 133.4, 142.7, 158.5, 171.4, 172.6. IR
1
1
1
1
2
1
H), 1.24 (t, J = 7.2 Hz, 3H), 1.19 (m, 6H). 13C-NMR (100 MHz, CDCl
): δ
3
4.2, 14.3, 16.4, 36.3, 48.0, 55.2, 56.0, 62.1, 62.2, 82.4, 113.2, 124.8,
25.2, 125.3, 125.8, 127.4, 128.7, 129.3, 130.3, 130.9, 131.1, 135.4, 158.2,
65.4, 171.2, 172.4. IR (CHCl
907, 2837, 1725, 1592, 1517, 1464, 1444, 1423, 1370, 1258, 1185, 1145,
-
1
3
(CHCl ): max (cm ) 3510 (broad OH), 3058, 2932, 2876, 1727, 1696, 1513,
1466, 1381, 1251, 1181, 1097, 1037, 858, 832, 812, 745, 703. HRMS (ESI)
-
1
+
3
): max (cm ) 3512 (broad OH), 3311, 2983,
m/z: [M+Na] calcd. for C29
32 6
H O Na 499.2091; found 499.2069.
+
097, 1026, 831, 810, 767, 747, 707. HRMS (ESI) m/z: [M+Na] Calcd. for
Diethyl
5-(4-methoxyphenyl)-2-(1-(naphthalen-2-
h,
value: 0.45 (EtOAc/Hexane) =1:10,
29 32 6
C H O Na 499.2091; found 499.2095.
yl)ethyl)dihydrofuran-3,3(2H)-di-carboxylate: Reaction time:
viscous liquid, 49 mg, yield: 30%, R
(v/v).
7
f
(2R,5R)-diethyl
5-(4-methoxyphenyl)-2-((R)-1-(naphthalen-1-
yl)ethyl)dihydrofuran-3,3(2H)-dicarboxylate: viscous liquid, 41 mg,
yield: 25%, R
f
value: 0.47 (EtOAc/Hexane) =1:10, (v/v).
1
5
h (cis, major): H-NMR (400 MHz, CDCl
3
): δ 7.68 - 7.65 (m, 4H), 7.39 -
7
.31 (m, 3H), 7.18 (d, J = 8.8Hz, 2H), 6.76 (d, J = 8.8 Hz, 2H), 4.72 (d, J =
1
5
7
7
g (cis, major): H -NMR (400 MHz, CDCl
3
): δ 8.15 (d, J = 8.2 Hz, 1H),
6.9 Hz, 1H), 4.63 (dd, J = 9.3, 6.9 Hz, 1H), 4.23 (q, J = 7.2 Hz, 2H), 3.87
(q, J = 7.2 Hz, 2H), 3.71 (s, 3H), 3.29 (t, J = 7.2 Hz, 1H), 2.58 (dd, J = 11.5,
6.9 Hz, 2H), 1.39 (d, J = 7.2 Hz, 3H), 1.25 (t, J = 7.2 Hz, 3H), 1.07 (t, J =
7.2 Hz, 3H). 13C-NMR (100 MHz, CDCl
55.4, 61.7, 61.9, 78.7, 87.4, 113.7, 125.3, 125.7, 126.4, 126.6, 127.4,
127.7, 127.8, 127.9, 132.4, 132.7, 133.5, 135.4, 141.6, 169.7, 171.4. IR
(CHCl
1370, 1249, 1175, 1096, 1037, 862, 831, 798, 746, 706, 667. HRMS (ESI)
m/z: [M+Na] calcd. for C29
.83 (d, J = 8.2 Hz, 1H), 7.68 (d, J = 8.2 Hz, 1H), 7.65 (d, J = 8.2 Hz, 1H),
.56 – 7.52 (m, 1H), 7.48 – 7.41 (m, 4H), 6.94 (d, J = 8.7 Hz, 2H), 5.28 (d,
J = 6.3 Hz, 1H), 4.77 (dd, J = 10.6, 5.6 Hz, 1H), 4.22 (q, J = 7.2 Hz, 2H),
.08 (m, 1H), 3.83 (s, 3H), 3.69 (q, J = 7.2 Hz, 1H), 3.22 (q, 1H), 2.76 (dd,
J = 10.6, 5.6 Hz, 2H), 1.44 (d, J = 7.2 Hz, 3H), 1.23 (t, J = 7.2 Hz, 3H), 0.92
t, J =7.2 Hz, 3H). 13C-NMR (100 MHz, CDCl
): δ 13.6, 14.1, 18.9, 37.8,
4.0, 55.5, 61.7, 61.9, 64.1, 78.9, 85.1, 114.0, 123.4, 125.4, 125.7, 126.0,
26.8, 127.1, 127.8, 128.9, 131.3, 132.6, 134.0, 141.0, 159.5, 169.4, 171.2.
3
): δ 13.8, 14.2, 21.2, 41.7, 44.1,
4
-1
(
4
1
3
3
): max (cm ) 3022, 2964, 2940, 2896, 1763, 1667, 1514, 1464,
+
32 6
H O Na 499.2091; found 499.2070.
-
1
IR (CHCl ): max (cm ) 3032, 2964, 2939, 2896, 1723, 1685, 1514, 1464,
3
1
370, 1249, 1175, 1096, 1037, 862, 831, 798, 746, 706. HRMS (ESI) m/z:
1
5
-
=
h (trans, minor): H-NMR (400 MHz, CDCl
3
): δ 7.74 - 7.71 (m, 4H), 7.49
+
[M+Na] calcd. for C29
32 6
H O Na 499.2091; found 499.2077.
7.41 (m, 3H), 6.98 (d, J = 8.8 Hz, 2H), 6.69 (d, J = 8.8 Hz, 2H), 5.13 (t, J
7.3 Hz, 1H), 4.49 (d, J = 8.2 Hz, 1H), 4.13 (q, J = 7.2 Hz, 2H), 3.84 (q, J
= 7.2 Hz, 2H), 3.68 (s, 3H), 3.21 (t, J = 7.5 Hz, 1H), 3.05 (dd, J = 12.9, 7.3
Hz, 1H), 2.21 (dd, J = 12.9, 7.8 Hz, 1H), 1.35 (d, J = 7.5 Hz, 3H), 1.22 -
1.16 (m, 6H). 13C-NMR (100 MHz, CDCl
1
5
7
2
g (trans, minor): H-NMR (400 MHz, CDCl
.89 (d, J = 8.9 Hz, 1H), 7.68 - 7. 64 (m, 2H), 7.55 (m, 1H), 7.48 - 7.44 (m,
H), 7.31 (d, J = 9.02 Hz, 2H), 6.87 (d, J = 9.02 Hz, 2H), 5.45 (d, J = 7.3
3
): δ 8.18 (d, J = 8.9 Hz, 1H),
3
): δ 14.0, 14.1, 20.9, 42.4, 44.1,
Hz , 1H), 5.39 (t, J = , 7.5 Hz 1H), 4.05 (q, J = 7.2 Hz, 2H), 3.79 (s, 3H),
55.4, 60.5, 61.6, 78.1, 86.9, 113.8, 125.3, 125.8, 126.5, 126.6, 127.1,
127.5, 128.9, 132.1, 132.5, 133.6, 137.7, 154.8, 169.7, 170.2.
3.73 (q, J = 7.2 Hz, 1H), 3.63 (m, 1H), 3.26 (q, J = 7.2 Hz, 1H), 3.16 (dd, J
= 10.5, 7.3 Hz, 1H), 2.41 (dd, J = 13.5, 7.3 Hz, 1H), 1.41 (d, J = 7.2 Hz,
3
H), 1.08 (t, J = 7.2 Hz, 3H), 0.87 (t, J = 7.2 Hz, 3H). 13C-NMR (100 MHz,
(2S,4S)-diethyl 2-hydroxy-4-(4-methoxyphenyl)-3-(4-nitrophenyl)-3-
CDCl
1
1
3
): δ 13.5, 13.9, 19.4, 35.8, 44.1, 55.4, 61.6, 61.8, 63.9, 79.1, 85.8,
14.8, 123.1, 124.5, 125.4, 125.8, 127.0, 128.0, 128.8, 131.3, 132.8, 134.4,
41.1, 159.1, 169.5, 170.5.
phenylcyclope-ntane-1,1-dicarboxylate (3i): Reaction time: 1 h, 1a (100
mg, 0.34 mmol), 2e (99 mg, 0.41 mmol), white solid, m.p. 190 °C, 105 mg,
1
yield: 58%, R
CDCl
.07 (d, J = 8.8 Hz, 2H), 7.02 (d, J = 8.6 Hz, 2H), 6.55 (d, J = 8.6 Hz, 2H),
f
value: 0.31 (EtOAc/Hexane) =1:10 (v/v). H -NMR (400 MHz,
3
): δ 7.83 (d, J = 8.8 Hz, 2H), 7.3 – 7.27 (m, 3H), 7.28 – 7.21 (m, 2H),
7
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