[CH2:1]=[CH:2][CH2:3][CH2:4]CC.[C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19])(=[O:9])[CH3:8]>>[C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:1][CH2:2][CH2:3][CH3:4])(=[O:9])[CH3:8]Reactions between 1-hexene and 8-nonenyl acetate were conducted using methods analogous to those described above using to form the pheromone derivative 17. When catalyzed by Ruthenium complex 1, the reaction proceeded in good yield (67%) with high Z-selectivity (91%) at a low catalyst loading (0.5 mol %).
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