1: With trimethylboroxine; (R)-(-)-α,α-diphenyl-2-pyrrolidinemethanol in toluene T=20 - 150°C; 2: 8-(benzyloxy)-5-(2-bromoacetyl)quinolin-2(1H)-one With borane in tetrahydrofuran; toluene T=-10°C; 4.75 h; 3: With methanol in tetrahydrofuran; toluene T=-10°C;

1: (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole With borane dimethyl sulfide complex in tetrahydrofuran T=0°C; 0.166667 h; 2: 8-benzyloxy-5-bromoacetylcarbostyril in tetrahydrofuran T=-10°C; 0.333333 h; 3: With borane dimethyl sulfide complex T=0°C; 5 h;

1.1: pyridinium tribromide / tetrahydrofuran / 0 °C / Reflux 2.1: (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / tetrahydrofuran / 0.67 h / -55 - -45 °C / Inert atmosphere 2.2: -45 - 0 °C / Inert atmosphere 2.3: 20 °C View Scheme

1.1: 2.5 h / 70 °C / Cooling with ice 2.1: AlCl3, aluminium chloride / anhydrous dichloroethane / 3 h / 80 °C / Cooling with ice 2.2: 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 4.1: pyridinium tribromide / tetrahydrofuran / 0 °C / Reflux 5.1: (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / tetrahydrofuran / 0.67 h / -55 - -45 °C / Inert atmosphere 5.2: -45 - 0 °C / Inert atmosphere 5.3: 20 °C View Scheme

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Cooling with ice 2.1: 2.5 h / 70 °C / Cooling with ice 3.1: AlCl3, aluminium chloride / anhydrous dichloroethane / 3 h / 80 °C / Cooling with ice 3.2: 20 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 5.1: pyridinium tribromide / tetrahydrofuran / 0 °C / Reflux 6.1: (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / tetrahydrofuran / 0.67 h / -55 - -45 °C / Inert atmosphere 6.2: -45 - 0 °C / Inert atmosphere 6.3: 20 °C View Scheme

1.1: AlCl3, aluminium chloride / anhydrous dichloroethane / 3 h / 80 °C / Cooling with ice 1.2: 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 3.1: pyridinium tribromide / tetrahydrofuran / 0 °C / Reflux 4.1: (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / tetrahydrofuran / 0.67 h / -55 - -45 °C / Inert atmosphere 4.2: -45 - 0 °C / Inert atmosphere 4.3: 20 °C View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: pyridinium tribromide / tetrahydrofuran / 0 °C / Reflux 3.1: (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / tetrahydrofuran / 0.67 h / -55 - -45 °C / Inert atmosphere 3.2: -45 - 0 °C / Inert atmosphere 3.3: 20 °C View Scheme

1.1: toluene-4-sulfonic acid; vinyl 1-butyl ether / tetrahydrofuran; toluene / 0.5 h / 20 - 25 °C / |Molecular sieve 1.2: 100 °C 2.1: 5 palladium on charcoal; hydrogen / methanol / 225.02 Torr / |Inert atmosphere View Scheme

potassium carbonate in water; acetone 2.5 h; Heating / reflux; Product distribution / selectivity;