Reaction Steps
Following the general procedure, phenyl pent-4-enoate (50.0 mg, 0.284 mmol) was treated with butyl vinyl ether (284 mg, 2.84 mmol) and 2.5 mol % of in situ-generated complex la (71.0 μL, 0.10 M, 7.09 μmol; final substrate concentration=4.0 M) and allowed to stir for 2 h. The unpurified product is 98% Z (as determined by 400 MHz 1H NMR analysis). The resulting oil was purified by silica gel chromatography (50:1 hexanes:Et2O) to afford 8c (55.6 mg, 0.224 mmol, 79.0% yield, >98% Z isomer) as a colorless oil. IR (neat): 3040 (w), 2959 (m), 2933 (m), 2872 (m), 1759 (s), 1663 (m), 1594 (m), 1493 (m), 1374 (m), 1359 (m), 1272 (m), 1227 (m), 1195 (s), 1162 (s), 1130 (s), 1102 (s), 1072 (m); 1H NMR (400 MHz, CDCl3): δ 7.40-7.34 (2H, m), 7.25-7.19 (1H, m), 7.11-7.07 (2H, m), [diagnostic E isomer signal: 6.37 (1H, d, J=12.8 Hz)], 6.02 (1H, dt, J=6.0, 1.2 Hz), 4.43 (1H, td, J=6.8, 6.4 Hz), 3.75 (2H, t, J=6.4 Hz), 2.66-2.60 (2H, m), 2.56-2.49 (2H, m), 1.65-1.57 (2H, m), 1.46-1.35 (2H, m), 0.94 (3H, t, J=7.4 Hz); 13H NMR (100 MHz, CDCl3): δ 172.0, 150.9, 146.4, 129.4, 125.7, 121.7, 103.8, 72.2, 34.7, 32.0, 19.9, 19.1, 13.9; HRMS (ESI+) [M+H]+ calcd for C15H21O3: 249.1491, found: 249.1500.
