1: With N-ethyl-N,N-diisopropylamine; bis[(1S,2R,3S,5S)-pinan-3-yl]chloroborane in dichloromethane T=-5 - 0°C; 3.75 - 4.75 h; 2: With triethanolamine in dichloromethane T=20 - 30°C; 2 h;

sodium formate; [(R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine](p-cymene)ruthenium; Aliquatreg; 336 in dichloromethane; water T=40°C; 60 h; Inert atmosphere; Product distribution / selectivity;

hydrogenchloride; sodium chloride in tetrahydrofuran

1: 92 percent / toluene; tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h View Scheme

1: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 2: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h View Scheme

1: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 2: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h View Scheme

1: diisopropyl ethyl amine / CH2Cl2 / 0 - 35 °C 2: sodium methoxide / CH2Cl2; dimethylformamide / Heating 3: tetrahydrofuran; toluene / 0 - 5 °C View Scheme

1: in toluene T=-5 - 15°C; 18 h; 2: With water; sodium hydrogencarbonate in toluene T=20 - 30°C; 3 h;