n-butyllithium; potassium tert-butylate in tetrahydrofuran; hexane; dichloromethane soln. of (Z)-2-butene (87 mmol, THF, Ar) was treated with KO-t-Bu (85.2mmol) and n-BuLi (85.1 mmol) (hexane, -78°C, 15 min); addn. of FB(OMe)2 (89.4 mmol) for 1 h; extn. of crotylboronic acid (Et2O); addn. of pinacol (0.102 mmol); concn. gave an oil that was distd. (72-78°C, > 5 mm Hg); the product was 97percent isomeric purity;

1: methyl-1-propene With n-butyllithium; potassium tert-butylate in tetrahydrofuran; hexane T=-50°C; 0.5 h; 2: With tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78°C; 3: 2,3-dimethylbutane-2,3-diol With hydrogenchloride; sodium chloride in tetrahydrofuran

palladium dichloride in tetrahydrofuran T=60°C; 12 h; optical yield given as percent destereoselective reaction;

palladium dichloride in tetrahydrofuran T=60°C; 12 h; optical yield given as percent destereoselective reaction;

1: [Rh(nbd)(CH3CN)2]SbF6; bis(1,1-diphenylphosphino)methane / 1,2-dichloro-ethane / 0.33 h / 90 °C / Inert atmosphere 2: [Rh(nbd)(CH3CN)2]SbF6; bis(1,1-diphenylphosphino)methane / 1,2-dichloro-ethane / 6 h / 90 °C / Inert atmosphere View Scheme

1: magnesium sulfate / dichloromethane / 20 °C / Inert atmosphere 2: [Rh(nbd)(CH3CN)2]SbF6; bis(1,1-diphenylphosphino)methane / 1,2-dichloro-ethane / 6 h / 90 °C / Inert atmosphere 3: [Rh(nbd)(CH3CN)2]SbF6; bis(1,1-diphenylphosphino)methane / 1,2-dichloro-ethane / 0.33 h / 90 °C / Inert atmosphere 4: [Rh(nbd)(CH3CN)2]SbF6; bis(1,1-diphenylphosphino)methane / 1,2-dichloro-ethane / 6 h / 90 °C / Inert atmosphere View Scheme

[Ir(cod)2]BF4; C44H45O4P; hydrogen; tri-cyclo-hexyl-phosphine in 1,2-dichloro-ethane T=28°C; 5.33 h; Molecular sieve;

in diethyl ether at -78 to 23°C under Ar; various product ratios for various amts. of org. compd.;

in tetrahydrofuran at -78 to 23°C under Ar;

[Rh(nbd)(CH3CN)2]SbF6; bis(1,1-diphenylphosphino)methane in 1,2-dichloro-ethane T=90°C; 6 h; Inert atmosphere; optical yield given as percent de;