1: crotonaldehyde With (S)-5-benzyl-2,2,3-trimethylimidazolidine-4-thione; trifluoroacetic acid in tetrahydrofuran; isopropyl alcohol T=20°C; Friedel-Crafts alkylation; 0.25 h; 2: 1-methyl-1H-indole in tetrahydrofuran; isopropyl alcohol T=-25°C; Friedel-Crafts alkylation; 5 h; optical yield given as percent eeenantioselective reaction;

1: With methyl iodide in ethyl acetate T=50°C; 2: With sodium hydroxide in benzene T=80°C; Further stages.;

trifluoroacetic acid; MacMillan imidazolidinone in dichloromethane; water T=-83°C; Friedel-Crafts alkylation; 31 h; Product distribution; Further Variations:Reaction partnersTemperaturesSolventsCatalyststime;

1: NaBH4 / methanol / 1.5 h / 20 °C 2: ethyl acetate / 14 h / 50 °C 3: 170 mg / aq. 6-amino-1-caproic acid hydrochloride / benzene / 5 h / 80 °C View Scheme

1: 97 percent / Sc(III)-(S,S)-inda-pybox)(OTf)3; molecular sieves 4 Angstroem / acetonitrile / 24 h / -40 °C 2: NaBH4 / methanol / 1.5 h / 20 °C 3: ethyl acetate / 14 h / 50 °C 4: 170 mg / aq. 6-amino-1-caproic acid hydrochloride / benzene / 5 h / 80 °C View Scheme

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