[Ph2C3H3N2(C6H3(Me)Ph)(C6H3Et2)]BF4; copper(l) chloride; sodium t-butanolate in tetrahydrofuran T=-78°C; 1 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

hydrogenchloride in diethyl ether 1.) -70 deg C, 10 min; Yield given;

(CuOTf)2.C6H6 in ethylene glycol dimethyl ether T=0°C; 8 h; Title compound not separated from byproducts.;

1.1: n-BuLi / hexane; tetrahydrofuran / -78 - 22 °C 1.2: tetrahydrofuran; hexane / -78 - 22 °C 2.1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene; diethyl ether / 0 - 22 °C 3.1: Dess-Martin periodinane / CH2Cl2 / 22 °C 4.1: (CuOTf)2*C6H6; trans-(S)-nBuNHC(O)CH(i-Pr)N=CH-(o-Ph2P)Ph / 1,2-dimethoxy-ethane / 8 h / 0 °C View Scheme

1: Dess-Martin periodinane / CH2Cl2 / 22 °C 2: (CuOTf)2*C6H6; trans-(S)-nBuNHC(O)CH(i-Pr)N=CH-(o-Ph2P)Ph / 1,2-dimethoxy-ethane / 8 h / 0 °C View Scheme

BF4(1-)*C41H35N2(1+); 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran; water T=22°C; 12 h; Inert atmosphere; optical yield given as percent ee;

BF4(1-)*C41H35N2(1+); 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran; water T=22°C; 12 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

methyllithium; (R)-(2,2'-bis(diphenylphosphino)-1,1'- binaphthyl)palladium (II) chloride 1.) benzene, 80 degC, 17 h; 2.) benzene, ether, -70 degC, 10 min; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

methyllithium; Pd[(S)-binap]Cl2 in diethyl ether; benzene effect of the catalyst; Product distribution;