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W. Adam et al.
PAPER
H), 6.69 (d, J = 7.9 Hz, 1 H), 6.70–6.89 (m, 2 H), 7.01–7.25 (m, 10
H), 7.37–7.43 (m, 1 H), 7.58–7.61 (m, 3 H).
13C NMR (63 MHz, CDCl3): d = 21.3 (+), 21.4 (+), 56.1 (+), 57.6
(+), 71.6 (+), 125.1 (+), 126.4 (+), 127.3 (+), 128.0 (+), 128.6 (+),
128.7 (+), 128.9 (+), 129.0 (+), 129.6 (+), 130.7 (+), 133.3 (+),
134.0, 134.3, 135.5, 137.9, 142.6, 143.2, 144.7, 198.6.
1H NMR (400 MHz, CDCl3): d = 2.21 (s, 3 H), 4.10 (d, J = 7.7 Hz,
1 H), 4.41–4.45 (m, 1 H), 5.65 (d, J = 7.1 Hz, 1 H), 6.71 (d, J = 7.6
Hz, 1 H), 6.76 and 6.88 (AA¢BB¢ system, 4 H), 7.07–7.26 (m, 10 H),
7.66–7.72 (m, 3 H).
13C NMR (100 MHz, CDCl3): d = 21.5 (q), 56.3 (d), 56.9 (d), 71.5
(d), 125.5 (d), 126.0 (d), 127.4 (d), 128.0 (d), 128.6 (d), 128.7 (d),
128.9 (d), 129.0 (d), 129.1 (d), 129.2 (d), 129.7 (d), 130.5 (d), 133.0
(s), 134.0 (s), 142.5 (s), 142.6 (s), 144.4 (s), 146.2 (s), 197.8 (s).
Anal. Calcd for C30H26O3S (466.16): C, 77.22; H, 5.62; S, 6.97.
Found: C, 77.10; H, 5.55; S, 6.95.
+
HRMS [CI (NH3)]: m/z [M + NH4]+ calcd for C29H24O3S·NH4 :
Reaction of Ylide 1a with a,b-Enone 3b
470.1790; found: 470.1787.
A suspension of ylide 1a (0.5 g, 1.0 mmol) and (E)-4-phenylbut-3-
en-2-one (3b; 0.35 g, 2.4 mmol) in the presence of a catalytic
amount of Rh2(OAc)4 in MeCN (10 mL) was stirred for 84 h accord-
ing to the above general procedure. The solvent was evaporated
(20 °C/15 Torr) and the residue was chromatographed on silica gel
(CH2Cl2–PE) to yield 1-[1-phenyl-3-(phenylsulfonyl)indan-2-
yl]ethanone (4c; 67.0 mg, 18%) as colorless needles; mp 115–
116 °C (CHCl3–PE).
Reaction of Ylide 1b with Chalcone 3d
A suspension of ylide 1b (0.53 g, 1.0 mmol) and (E)-3-phenyl-1-(4-
tolyl)prop-2-en-1-one (3d; 0.68 g, 3.1 mmol) in CH2Cl2 (10 mL)
was stirred for 12 h according to the above general procedure. The
solvent was evaporated (20 °C/15 Torr) and the residue was chro-
matographed on silica gel (CH2Cl2–PE) to yield [5-methyl-1-phe-
nyl-3-(4-tolylsulfonyl)indan-2-yl](4-tolyl)methanone (4f; 200 mg,
41%) as colorless needles; mp 196–199 °C (EtOH).
IR (KBr): 2940, 1760, 1470, 1390, 1375, 1335, 1310, 1245, 1230,
1205, 1180, 1150, 1105, 1095, 1040, 1015, 830, 780, 745 cm–1.
1H NMR (400 MHz, CDCl3): d = 1.98 (s, 3 H), 3.76 (t, J = 7.4 Hz,
1 H), 4.25 (d, J = 7.4 Hz, 1 H), 5.48 (d, J = 7.4 Hz, 1 H), 6.78 (d,
J = 7.4 Hz, 1 H), 6.93–6.95 (m, 2 H), 7.25–7.33 (m, 5 H), 7.50–7.53
(m, 2 H), 7.64–7.69 (m, 2 H), 7.82–7.84 (m, 2 H).
13C NMR (100 MHz, CDCl3): d = 30.3 (q), 54.3 (d), 61.9 (d), 70.4
(d), 125.4 (d), 126.0 (d), 127.5 (d), 128.0 (d), 128.3 (d), 129.0 (d),
129.2 (d), 129.5 (d), 129.8 (d), 133.5 (s), 134.0 (d), 137.1 (s), 142.9
(s), 145.9 (s), 205.3 (s).
IR (KBr): 3049, 1678, 1595, 1491, 1448, 1382, 1316, 1299, 1238,
1147, 1110, 1085, 1022, 979, 891, 840, 814, 776, 716 cm–1.
1H NMR (250 MHz, CDCl3): d = 2.26 (s, 3 H), 2.32 (s, 3 H), 2.40
(s, 3 H), 4.15 (d, J = 7.5 Hz, 1 H), 4.49 (t, J = 7.5 Hz, 1 H), 5.68 (d,
J = 7.2 Hz, 1 H), 6.71 (d, J = 7.9 Hz, 1 H), 6.78 and 7.01 (AA¢BB¢
system, 4 H), 7.05 and 7.62 (AA¢BB¢ system, 4 H), 7.09–7.67 (m, 6
H), 7.94–8.00 (m, 1 H).
13C NMR (63 MHz, CDCl3): d = 21.0, 21.3, 21.4, 55.7, 57.5, 71.6,
125.0, 126.3, 127.9, 128.4, 128.7, 129.0, 129.3, 129.5, 130.6, 133.2,
133.9, 134.3, 135.5, 136.9, 137.8, 139.6, 143.4, 144.7, 198.7.
+
HRMS [CI (NH3)]: m/z [M + NH4]+ calcd for C23H20O3S·NH4 :
394.1477; found: 394.1481.
Anal. Calcd for C31H28O3S (480.18): C, 77.47; H, 5.87; S, 6.67.
Found: C, 77.20; H, 5.85; S, 6.75.
Reaction of Ylide 1b with a,b-Enone 3c
A suspension of ylide 1b (0.53 g, 1.0 mmol) and methyl cinnamate
(3c; 1.0 g, 6.2 mmol) in CH2Cl2 (5 mL) was stirred for 48 h accord-
ing to the above general procedure. The solvent was evaporated
(20 °C/15 Torr) and the residue was chromatographed on silica gel
(CH2Cl2–PE) to yield methyl 5-methyl-1-phenyl-3-(4-tolylsulfo-
nyl)indane-2-carboxylate (4d; 140 mg, 33%) as colorless needles;
mp 99–103 °C (PE).
Reaction of Ylide 1a with Chalcone 3e
A suspension of ylide 1a (0.436 g, 0.87 mmol) and (E)-1-(4-meth-
oxyphenyl)-3-phenylprop-2-en-1-one (3e; 0.50 g, 2.10 mmol) in the
presence of a catalytic amount of Rh2(OAc)4 in MeCN (10 mL) was
stirred for 132 h according to the above general procedure. The sol-
vent was evaporated (20 °C/15 Torr) and the residue was chromato-
graphed on silica gel (CH2Cl2–PE) to yield (4-methoxyphenyl)[1-
phenyl-3-(phenylsulfonyl)indan-2-yl]methanone (4g; 201 mg,
49%) as colorless plates; mp 149–150 °C (CHCl3–PE).
IR (KBr): 3066, 3032, 1735, 1596, 1493, 1440, 1378, 1340, 1299,
1240, 1130, 1083, 1041, 1008, 979, 889, 854, 830, 813 cm–1.
IR (KBr): 1715, 1635, 1610, 1540, 1515, 1475, 1440, 1365, 1330,
1275, 1260, 1235, 1195, 1160, 1130, 1100, 1030, 1005, 890, 860,
845, 775 cm–1.
1H NMR (250 MHz, CDCl3): d = 3.80 (s, 3 H), 4.21 (d, J = 7.5 Hz,
1 H), 4.46–4.53 (m, 1 H), 5.76 (d, J = 7.5 Hz, 1 H), 6.66 (d, J = 9.0
Hz, 2 H), 6.81–6.91 (m, 3 H), 7.16–7.51 (m, 10 H), 7.76–7.84 (m, 3
H).
13C NMR (100 MHz, CDCl3): d = 55.3 (+), 56.3 (+), 56.6 (+), 71.4
(+), 113.6 (+), 125.8 (+), 126.3 (+), 127.7 (+), 128.3 (+), 128.8,
129.0 (+), 129.1 (+), 129.3 (+), 129.5 (+), 130.0 (+), 131.6 (+),
134.1 (+), 134.4, 137.7, 143.0, 146.6, 164.4, 197.3.
1H NMR (250 MHz, CDCl3): d = 2.41 (s, 3 H), 2.42 (s, 3 H), 3.46
(t, J = 7.4 Hz, 1 H), 3.53 (s, 3 H), 4.38 (d, J = 7.5 Hz, 1 H), 5.35 (d,
J = 7.2 Hz, 1 H), 6.73 (d, J = 7.8 Hz, 1 H), 6.86–6.90 (m, 2 H),
7.10–7.27 (m, 6 H), 7.65–7.71 (m, 3 H).
13C NMR (63 MHz, CDCl3): d = 21.2 (+), 21.5 (+), 52.2 (+), 54.4
(+), 55.1 (+), 71.4 (+), 125.0 (+), 126.4 (+), 127.1 (+), 128.0 (+),
128.5 (+), 129.5 (+), 129.6 (+), 130.6 (+), 133.6, 133.7, 137.8,
142.6, 142.7, 144.8, 172.6.
Anal. Calcd for C25H24O4S (420.14): C, 71.40; H, 5.75; S, 7.63.
Found: C, 71.60; H, 5.65; S, 7.55.
Reaction of Ylide 1a with Chalcone 3d
HRMS (EI): m/z [M+] calcd for C29H24O4S: 468.1395; found:
468.1391.
A suspension of ylide 1a (0.187 g, 0.37 mmol) and (E)-3-phenyl-1-
(4-tolyl)prop-2-en-1-one (3d; 0.20 g, 0.90 mmol) in the presence of
a catalytic amount of Rh2(OAc)4 in MeCN (5 mL) was stirred for 18
h according to the above general procedure. The solvent was evap-
orated (20 °C/15 Torr) and the residue was chromatographed on sil-
ica gel (CH2Cl2–PE) to yield [1-phenyl-3-(phenylsulfonyl)indan-2-
yl](4-tolyl)methanone (4e; 92.0 mg, 54%) as colorless plates; mp
127–129 °C (CHCl3–PE).
Reaction of Ylide 1b with Chalcone 3e
A suspension of ylide 1b (0.53 g, 1.0 mmol) and (E)-1-(4-methoxy-
phenyl)-3-phenylprop-2-en-1-one (3e; 1.0 g, 4.2 mmol) in CH2Cl2
(10 mL) was stirred for 12 h according to the above general proce-
dure. The solvent was evaporated (20 °C/15 Torr) and the residue
was chromatographed on silica gel (CH2Cl2–PE) to yield (4-meth-
oxyphenyl)[5-methyl-1-phenyl-3-(4-tolylsulfonyl)indan-2-yl]meth-
IR (KBr): 3130, 3100, 1710, 1640, 1505, 1470, 1435, 1325, 1265,
1200, 1165, 1100, 1015, 935, 905, 840, 775 cm–1.
Synthesis 2007, No. 20, 3211–3218 © Thieme Stuttgart · New York