2
784
C. H. Oh et al.
LETTER
135.05, 132.60, 132.48, 132.09, 130.32, 129.64, 128.71,
monitored by TLC, the reaction mixture was concentrated in
vacuo and the residue was subjected to flash column
chromatography (hexane–EtOAc, 20:1) to afford the
corresponding product 3a (72.4 mg, 83%); FT-IR (NaCl):
128.68, 128.65, 128.56, 128.54, 128.52, 128.04, 127.02,
+
126.01, 94.70; HRMS: m/z calcd for C H ONa : 255.0786;
1
7
12
found: 255.0781. 3i: FT-IR (NaCl): 2958, 2928, 2865, 1962,
–
1 1
3
1
1
7
058, 2961, 2926, 2864, 2362, 2335, 1686, 1627, 1588,
1754, 1666, 1562, 1466, 1367, 1277, 1205 cm ; H NMR
–
1 1
491, 1452 cm ; H NMR (400 MHz, CDCl ): d = 8.00 (s,
(400 MHz, CDCl ): d = 8.04 (s, 1 H), 7.98–7.90 (m, 3 H),
3
3
H), 7.93 (d, J = 8.05 Hz, 1 H), 7.88 (d, J = 8.00 Hz, 1 H),
7.75–7.68 (m, 2 H), 7.66–7.53 (m, 2 H), 7.49–7.41 (m, 1 H),
1
3
.85 (s, 1 H), 7.61–7.51 (m, 2 H), 7.48–7.38 (m, 5 H), 2.35
7.39–7.28 (m, 5 H), 7.25–7.16 (m, 3 H); C NMR (100
(
(
t, J = 7.4 Hz, 2 H), 1.44 (quint, J = 7.4 Hz, 2 H), 1.18–1.06
m, 2 H), 0.74 (t, J = 7.4 Hz, 3 H); C NMR (100 MHz,
MHz, CDCl ): d = 198.57, 198.53, 140.56, 138.74, 137.93,
3
1
3
137.61, 134.29, 133.06, 131.78, 130.26, 129.67, 129.57,
129.43, 129.31, 128.65, 128.52, 128.35, 128.18, 128.05,
CDCl ): d = 207.88, 141.09, 139.85, 137.45, 134.15, 132.07,
1
3
+
29.49, 129.15, 129.03, 129.89, 128.82, 128.20, 128.04,
127.44, 127.04; HRMS: m/z calcd for C H ONa :
2
3
16
1
27.99, 127.86, 126.96, 42.88, 26,93, 22.36, 13.90; HRMS:
331.1099; found: 331.1110. 3j: FT-IR (NaCl): 3054, 2927,
2861, 2364, 2333, 1662, 1596, 1446, 1280, 1222 cm ; H
+
–1 1
m/z calcd for C H ONa : 311.1411; found: 311.1402. 3b:
2
1
20
FT-IR (NaCl): 2958, 2929, 2864, 1682, 1635, 1593, 1461
NMR (400 MHz, CDCl ): d = 8.18 (s, 1 H), 8.00 (d,
J = 10.46 Hz, 2 H), 7.94 (d, J = 7.94 Hz, 1 H), 7.78 (t,
J = 8.65, 8.65 Hz, 2 H), 7.72–7.59 (m, 3 H), 7.55–7.50 (m, 2
3
–
1 1
cm ; H NMR (400 MHz, CDCl ): d = 8.48 (s, 1 H), 8.11–
3
7.82 (m, 4 H), 7.58 (dddd, J = 18.31, 8.15, 6.86, 1.37 Hz, 2
H), 3.11 (t, J = 7.4 Hz, 2 H), 1.87–1.70 (m, 2 H), 1.52–1.41
H), 7.45–7.32 (m, 4 H), 7.32–7.25 (m, 2 H), 7.12 (t, J = 7.82
1
3
13
(
m, 2 H), 0.99 (t, J = 7.4 Hz, 2 H); C NMR (100 MHz,
Hz, 2 H); C NMR (100 MHz, CDCl ): d = 198.11, 138.63,
3
CDCl ): d = 200.55, 135.47, 134.39, 132.52, 129.71, 129.66,
138.19, 137.86, 136.87, 134.11, 133.58, 132.51, 132.19,
131.98, 130.96, 129.78, 129.69, 128.85, 128.33, 128.29,
3
129.58, 129.55, 129.50, 128.45, 128.35, 128.29, 127.79,
1
27.73, 126.67, 124.00, 123.94, 38.40, 26.63, 22.52, 13.97;
128.20, 128.15, 128.11, 128.04, 127.91, 127.17, 126.28,
+
+
HRMS: m/z calcd for C H ONa : 235.1099; found:
126.24, 125.87, 125.12; HRMS: m/z calcd for C H ONa :
1
5
16
27 18
2
35.1102. 3e: FT-IR (NaCl): 3051, 2991, 2957, 2927, 2870,
381.1255; found: 381.1263. 7e: FT-IR (NaCl): 3050, 2961,
–
1 1
1687, 1626, 1581, 1506, 1454, 1390 cm ; H NMR (400
2934, 2866, 2242, 1937, 1811, 1594, 1489, 1451, 1387, 1315
–
1 1
MHz, CDCl ): d = 8.19 (s, 1 H), 8.08–7.82 (m, 5 H), 7.73–
cm ; H NMR (400 MHz, CDCl ): d = 8.04 (s, 1 H), 7.98–
3
3
7.34 (m, 7 H), 2.31–2.10 (m, 2 H), 1.30–1.13 (m, 2 H), 0.98–
7.90 (m, 3 H), 7.75–7.68 (m, 2 H), 7.66–7.53 (m, 2 H), 7.49–
7.41 (m, 1 H), 7.39–7.28 (m, 5 H), 7.25–7.16 (m, 3 H), 3.10
(m, 2 H), 2.22 (td, J = 12.4, 4.4 Hz, 1 H), 2.08 (dt, J = 12.4,
4.4 Hz, 1 H), 1.23–1.15 (m, 4 H), 0.92 (m, 3 H), 0.51 (t,
1
3
0.80 (m, 2 H), 0.58 (t, J = 7.3 Hz, 3 H); C NMR (100 MHz,
CDCl ): d = 206.20, 140.32, 139.01, 135.76, 134.19, 133.83,
3
1
1
1
32.39, 132.32, 130.97, 129.04, 128.60, 128.57, 128.39,
28.22, 128.02, 127.73, 127.11, 126.69, 126.26, 126.06,
25.54, 41.96, 26.69, 22.20, 13.78; HRMS: m/z calcd for
1
3
J = 7.4 Hz, 3 H); C NMR (100 MHz, CDCl ): d = 198.57,
3
198.53, 140.56, 138.74, 137.93, 137.61, 134.29, 133.06,
131.78, 130.26, 129.67, 129.57, 129.43, 129.31, 128.65,
+
C H ONa : 361.1568; found: 361.1577. 3f: FT-IR (NaCl):
25
22
3
056, 2965, 2905, 2865, 1686, 1597, 1485, 1477, 1451,
128.52, 128.35, 128.18, 128.05, 127.44, 127.04; HRMS:
–
1
1
+
1
362, 1274 cm ; H NMR (400 MHz, CDCl ): d = 7.88
m/z calcd for C H ONa : 389.1881; found: 389.1890.
3
27 26
(
(
ddd, J = 9.37, 7.48, 3.72 Hz, 3 H), 7.62 (s, 1 H), 7.57–7.51
m, 2 H), 7.50–7.45 (m, 2 H), 7.45–7.33 (m, 3 H), 0.93 (s, 9
(8) For Au- or Ag-catalyzed [3,3]-sigmatropic rearrangement of
propargylic acetates, see: (a) Zhang, L.; Wang, S. J. Am.
Chem. Soc. 2006, 128, 1442. (b) Zhang, L. J. Am. Chem.
Soc. 2005, 127, 16804. (c) Buzas, A.; Istrate, F.; Gagosz, F.
Org. Lett. 2006, 8, 1957. (d) Sromek, A. W.; Kelin, A. V.;
Gevorgyan, V. Angew. Chem. Int. Ed. 2004, 43, 2280.
(9) (a) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.;
Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650.
(b) Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc.
2004, 126, 11164.
1
3
H); C NMR (100 MHz, CDCl ): d = 216.76, 141.18,
3
1
1
4
40.04, 136.40, 133.32, 131.75, 130.11, 130.02, 128.95,
28.83, 128.73, 128.12, 127.82, 127.19, 126.89, 125.17,
5.26, 27.57; HRMS: m/z calcd for C H ONa : 311.1412;
+
2
1
20
found: 311.1417. 3h: FT-IR (NaCl): 3059, 1651, 1624,
–
1 1
1597, 1465, 1442, 1380, 1349, 1283, 1233 cm ; H NMR
(
400 MHz, CDCl ): d = 8.28 (s, 1 H), 7.99–7.90 (m, 4 H),
3
7
.89–7.85 (m, 2 H), 7.67–7.60 (m, 2 H), 7.59–7.50 (m, 5 H);
13
C NMR (100 MHz, CDCl ): d = 196.97, 138.13, 135.49,
(10) Shah, B. K.; Neckers, D. C. Chem. Mater. 2006, 18, 603.
3
Synlett 2006, No. 17, 2781–2784 © Thieme Stuttgart · New York