1: cyanomethyl-phosphonic acid diethyl ester With sodium hydride in tetrahydrofuran; mineral oil T=20°C; Horner-Wadsworth-Emmons olefination; 0.5 h; 2: 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one in tetrahydrofuran; mineral oil T=40°C; Horner-Wadsworth-Emmons olefination; 1 h;

piperidine T=100 - 110°C;

tetrabutyl ammonium fluoride in tetrahydrofuran T=25 - 40°C; Product distribution / selectivity;

1.1: potassium carbonate / acetone / 5 h / Reflux 2.1: N,N-dimethyl-aniline / Inert atmosphere; Reflux 2.2: 25 °C 3.1: ozone / dichloromethane / -78 - 20 °C / Inert atmosphere 3.2: 20 °C 4.1: toluene-4-sulfonic acid / toluene / 0.75 h / Reflux 5.1: hydrogen / triethylamine; 5 Pd(II)/C(eggshell) / ethanol; tetrahydrofuran / 24 h / 35 °C / 4500.45 - 5250.53 Torr 6.1: sodium methylate / tetrahydrofuran / 1 h / 20 °C 6.2: 2.25 h / 20 °C View Scheme

1.1: toluene-4-sulfonic acid / toluene / 0.75 h / Reflux 2.1: hydrogen / triethylamine; 5 Pd(II)/C(eggshell) / ethanol; tetrahydrofuran / 24 h / 35 °C / 4500.45 - 5250.53 Torr 3.1: sodium methylate / tetrahydrofuran / 1 h / 20 °C 3.2: 2.25 h / 20 °C View Scheme

1.1: hydrogen / triethylamine; 5 Pd(II)/C(eggshell) / ethanol; tetrahydrofuran / 24 h / 35 °C / 4500.45 - 5250.53 Torr 2.1: sodium methylate / tetrahydrofuran / 1 h / 20 °C 2.2: 2.25 h / 20 °C View Scheme

1: With ammonia; nickel in ethanol T=30 - 38°C; P=3677.86 Torr; 5 - 6 h; 2: With hydrogen; palladium 10 on activated carbon in ethanol T=35 - 38°C; P=3677.86 Torr; 2 - 3 h; Product distribution / selectivity;

1: sodium tetrahydroborate; nickel dichloride / methanol / 15 - 25 °C 2: CHIRAL PACK IA-3 / isopropyl alcohol; diethylamine; hexane / 25 °C / Resolution of racemate View Scheme

copper diacetate; (R)-1-(diphenylphosphano)-2-((S)-1-(dicyclohexylphosphano)ethyl)ferrocene * ethanol in toluene; tert-butyl alcohol T=0 - 20°C; Product distribution / selectivity;