cerium(III) chloride; methyllithium in tetrahydrofuran; diethyl ether T=-78°C; 1.5 h;

bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in dichloromethane Title compound not separated from byproducts;

1: methyllithium With cerium(III) chloride in tetrahydrofuran; diethyl ether T=-78°C; 2 h; 2: (E)-1,8-dimorpholinooct-4-ene-1,8-dione in tetrahydrofuran; diethyl ether T=-78°C; 1.5 h; Further stages.;

in toluene

ethene; [2-(1-methylethoxy-κO)phenylmethyl-κC](nitrato-κO,κO′){rel-(2R,5R,7S)-tricyclo[3.3.1.13,7]decane-2,1-diyl[3-(2,4,6-trimethylphenyl)-1-imidazolidinyl-2-ylidene]}ruthenium in tetrahydrofuran T=35°C; P=3800.26 Torr; 4 h; Sealed tube;

1: (Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester; 1,4-trans-dibromo-2-butene 2: hydrolysis; 3: decarboxylation;

Grubb's 2nd generation catalyst in dichloromethane T=20°C; Inert atmosphereReflux; optical yield given as percent de;

(i), (ii) (hydrolysis), (iii) (decarboxylation); Multistep reaction;

1: [2-(1-methylethoxy-κO)phenylmethyl-κC](nitrato-κO,κO′){rel-(2R,5R,7S)-tricyclo[3.3.1.13,7]decane-2,1-diyl[3-(2,4,6-trimethylphenyl)-1-imidazolidinyl-2-ylidene]}ruthenium; ethene / tetrahydrofuran / 4 h / 35 °C / 3800.26 Torr / |Sealed tube 2: RuCl2(tricyclohexylphosphine)2(benzylidene) / neat (no solvent) / 16 h / 35 °C / 30 Torr / |Schlenk technique; |Inert atmosphere; |Sealed tube View Scheme

RuCl2(tricyclohexylphosphine)2(benzylidene) in dichloromethane 6 h; Inert atmosphereReflux;