9090
V. Fiandanese et al. / Tetrahedron Letters 44 (2003) 9087–9090
MHz, CDCl3) 133.7, 127.9, 126.9, 122.4, 87.1, 78.6,
67.6, 65.0, 31.6, 28.8, 28.7, 28.2, 22.6, 19.6, 14.0; MS
m/z 230 (M+, 38), 215 (4), 201 (12), 187 (34), 173 (39),
160 (18), 153 (19), 147 (71), 146 (26), 145 (70), 132 (25),
128 (20), 121 (18), 115 (30), 102 (18), 101 (23), 97 (28),
93 (17), 87 (17), 79 (17), 75 (18), 69 (32), 63 (17), 55
(18), 51 (15), 45 (95), 43 (50), 41 (100%). (5c) yellowish
oil; wmax (neat) 3081, 3063, 2994, 2956, 2897, 2213,
1561, 1490, 1442, 1249, 1208, 972, 865, 839, 754, 688
cm−1; lH (500 MHz, CDCl3) 7.53–7.47 (2H, m), 7.38–
7.28 (3H, m), 6.69 (1H, d, J=19.3 Hz), 6.05 (1H, d,
J=19.3 Hz), 0.13 (9H, s); lC (125.7 MHz, CDCl3)
149.9, 132.4, 129.1, 128.3, 122.0, 121.8, 81.9, 81.7, 74.2,
74.0, −1.8; MS m/z 224 (M+, 25), 210 (21), 209 (100),
184 (14), 183 (71), 169 (6), 155 (5), 153 (7), 129 (12), 105
(10), 98 (5), 92 (21), 77 (11), 73 (11), 59 (28), 53 (14), 45
(30), 43 (40%). (5e) whitish solid (petroleum ether, mp
116–118°C); wmax (KBr) 3104, 2957, 2898, 2208, 1593,
1518, 1342, 1251, 1105, 982, 974, 867, 852, 842, 747,
684 cm−1; lH (500 MHz, CDCl3) 8.16 (2H, d, J=8.9
Hz), 7.59 (2H, d, J=8.9 Hz), 6.72 (1H, d, J=19.3 Hz),
6.01 (1H, d, J=19.3 Hz), 0.09 (9H, s); lC (125.7 MHz,
CDCl3) 151.8, 147.3, 133.1, 128.7, 123.6, 121.3, 84.4,
79.4, 78.9, 73.2, −1.9; MS m/z 269 (M+, 19), 255 (21),
254 (100), 229 (11), 228 (53), 214 (6), 208 (8), 182 (21),
167 (10), 165 (5), 115 (4), 91 (7), 73 (14), 59 (63), 53
(10), 45 (34), 43 (33%). (5f) brown oil; wmax (neat) 3060,
3029, 2957, 2898, 2196, 1561, 1491, 1448, 1249, 972,
951, 864, 840, 747, 690 cm−1; lH (500 MHz, CDCl3)
7.44–7.28 (5H, m); 7.10 (1H, d, J=16.2 Hz), 6.69 (1H,
d, J=19.2 Hz), 6.27 (1H, d, J=16.2 Hz), 6.08 (1H, d,
J=19.2 Hz), 0.16 (9H, s); lC (125.7 MHz, CDCl3)
149.6, 144.3, 135.6, 129.1, 128.6, 126.3, 122.1, 106.8,
82.3, 81.8, 76.2, 74.6, −1.9; MS m/z 250 (M+, 46), 235
(48), 233 (21), 219 (15), 210 (12), 209 (56), 207 (11), 205
(12), 195 (15), 191 (15), 181 (10), 179 (12), 169 (19), 165
(22), 155 (14), 145 (9), 135 (10), 105 (16), 103 (11), 83
(12), 73 (100), 59 (93), 53 (22), 45 (59), 43 (81%).
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This work was financially supported by the Ministero
dell’Istruzione, dell’Universita` e della Ricerca (MIUR),
Rome, and the University of Bari (National Project
‘Stereoselezione in Sintesi Organica. Metodologie ed
Applicazioni’).
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