1: With N-ethyl-N,N-diisopropylamine; B-chloro-diisopinocampheylborane in dichloromethane T=-5 - 0°C; 3.75 - 4.75 h; 2: With triethanolamine in dichloromethane T=20 - 30°C; 2 h;

triethylamine; palladium diacetate; tris-(o-tolyl)phosphine in N,N-dimethyl-formamide T=100°C; Heck Reaction; 3 h;

1: (-)-sparteine; O2; Cs2CO3 / Pd(nbd)Cl2 / toluene; 2-methyl-propan-2-ol / 4.5 h / 80 °C / 760.05 Torr 2: P(o-tolyl)3; Et3N / Pd(OAc)2 / dimethylformamide / 3 h / 100 °C View Scheme

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

formic acid; caesium carbonate in N,N-dimethyl-formamide T=40°C; 24 h; Product distribution / selectivity;

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: methyl-magnesium chloride With cerium(III) chloride in tetrahydrofuran T=-5 - 0°C; 2.5 h; 2: lt;S-(E)gt;-2-lt;3-lt;3-lt;2-(7-chloro-2-quinolinyl)ethenylgt;phenylgt;-3-hydroxypropylgt;benzoic acid methyl ester in tetrahydrofuran; toluene T=3 - 5°C; 2.25 h; 3: With water; sodium carbonate; acetic acid more than 3 stages;

1: lt;S-(E)gt;-2-lt;3-lt;3-lt;2-(7-chloro-2-quinolinyl)ethenylgt;phenylgt;-3-hydroxypropylgt;benzoic acid methyl ester With Lanthanum chloride; lithium chloride in tetrahydrofuran T=20°C; 1 h; 2: methyl-magnesium chloride in tetrahydrofuran T=-5 - 0°C; 12 h; 3: With water; ammonium chloride in tetrahydrofuran T=20 - 25°C; Product distribution / selectivity;

cerium(III) chloride in tetrahydrofuran; toluene T=0°C; Grignard addition; 2 h; Product distribution; Further Variations:Reaction partnerscatalyst crystal habit;