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18 Troisi, L.; Fabio, M.; Rosato, F.;
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20 Reaction conducted according to general
procedure.
21 Reaction conducted using benzonitrile
as solvent (10 mL) for 15 h according to the general procedure.
Yields, after chromatographic purification, were about 80%.
23 Compound 1:
Crude product was purified by flash chromatography on silica gel
deactivated with Et3N (PE-Et2O, 8:2). ¹H
NMR (400 MHz, CDCl3): δ = 1.23
(s, 9 H), 6.11 (s, 1 H), 7.25-7.54 (m, 8 H), 7.98 (d, J = 8.1 Hz,
2 H). ¹³C NMR (100.62 MHz, CDCl3): δ = 25.0,
60.4, 85.8, 125.3, 126.6, 126.9, 128.0, 128.5, 131.9, 141.6, 161.4.
GC-MS (70 eV): m/z = 280
(<1) [M+], 177 (50),
121 (35), 105 (20), 77 (25), 57 (100). FTIR (CHCl3):
3067, 2987, 2927, 2852, 1656, 1494, 1452, 1326 cm-¹.
Anal. Calcd for C18H20N2O: C, 77.11;
H, 7.19; O, 5.71. Found: C, 77.09; H, 7.18; O, 5.69.
25 Diastereomeric ratio determined by ¹H
NMR on the crude product.