Ru(Η6-cymene)(MsDPEN)(BArF); hydrogen in dichloromethane T=40°C; P=38002.6 Torr; 10 h; Inert atmosphereAutoclave; optical yield given as percent eeenantioselective reaction;

1: tert-butyl (4-oxo-4-phenyl-butyl)-carbamate With formic acid T=20°C; 12 h; 2: With sodium hydrogencarbonate 6 h; 3: di-tert-butyl dicarbonate With Ru(Η6-cymene)(MsDPEN)(BArF); hydrogen in dichloromethane T=40°C; P=38002.6 Torr; 10 h; Inert atmosphereAutoclave; optical yield given as percent ee;

1: N-Boc-pyrrolidine With sec.-butyllithium; (-)-sparteine in diethyl ether; cyclohexane T=-78°C; 3 h; Inert atmosphere; 2: With zinc(II) chloride in tetrahydrofuran; diethyl ether; cyclohexane T=-78 - 20°C; 1.08333 h; Inert atmosphere; 3: bromobenzene With palladium diacetate; [(t-Bu)3PH]BF4 in tetrahydrofuran; diethyl ether; cyclohexane T=20°C; 16 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

1: N-Boc-pyrrolidine With sec.-butyllithium; (-)-sparteine in cyclohexane T=-78 - -68°C; 3 h; 2: With zinc(II) chloride in diethyl ether; cyclohexane T=-74 - 20°C; 3: bromobenzene With palladium diacetate; [(t-Bu)3PH]BF4 in diethyl ether; cyclohexane T=20°C; Negishi coupling; Title compound not separated from byproducts;

sec.-butyllithium; (-)-sparteine in toluene T=-78°C; Yield given. Title compound not separated from byproducts;

Ru(Η6-cymene)(MsDPEN)(BArF); hydrogen in methanol T=40°C; P=38002.6 Torr; 10 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

1: N-Boc-pyrrolidine With sec.-butyllithium; (-)-sparteine in cyclohexane T=-78 - -68°C; 3 h; 2: With zinc(II) chloride in diethyl ether; cyclohexane T=-74 - 20°C; 3: chlorobenzene With palladium diacetate; [(t-Bu)3PH]BF4 in diethyl ether; cyclohexane T=20°C; Negishi coupling; Title compound not separated from byproducts;

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.75 h / -78 - 20 °C / Inert atmosphere 2.1: tetrahydrofuran / 3.5 h / -78 - 20 °C / Inert atmosphere 3.1: formic acid / 12 h / 20 °C 3.2: 6 h 3.3: 10 h / 40 °C / 38002.6 Torr / Inert atmosphere; Autoclave View Scheme

1: N-tert-butoxycarbonyl 2-lithiopyrrolidine With zinc(II) chloride in diethyl ether; tert-butyl methyl ether; cyclohexane T=-74°C; 0.5 h; Inert atmosphere; 2: bromobenzene With palladium diacetate; [(t-Bu)3PH]BF4 in diethyl ether; tert-butyl methyl ether; cyclohexane T=20°C; Negishi coupling reaction; 16 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

1: N-tert-butoxycarbonyl 2-lithiopyrrolidine With zinc(II) chloride in diethyl ether; tert-butyl methyl ether; cyclohexane T=-74°C; 0.5 h; Inert atmosphere; 2: iodobenzene With palladium diacetate; [(t-Bu)3PH]BF4 in diethyl ether; tert-butyl methyl ether; cyclohexane T=20°C; Negishi coupling reaction; 16 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;