whole cells of P. putida NCIMB 8859 (wild-type, with NDO); sodium 2-oxopropanoate; oxygen in phosphate buffer; ethanol T=30°C; pH=7.2; 24 h;

diisobutylaluminium hydride in diethyl ether; hexane 1) -78 deg C to room temperature, 2) room temperature, 8 h;

1: LiH / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temp., 48 h 2: 1.) t-BuOK, 2.) DIBAL-H / 1.) THF, -50 deg C, 10 min., 2.) Et2O, hexane, -78 to room temp., 12 h View Scheme

1: NaBH4 / methanol / Ambient temperature 2: toluene-p-sulfonic acid / toluene / 4 h / Heating 3: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -78 deg C to room temperature, 2) room temperature, 8 h View Scheme

1: 51.4 percent / NaBH4 / ethanol / 6 h 3: NaBH4 / methanol / Ambient temperature 4: toluene-p-sulfonic acid / toluene / 4 h / Heating 5: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -78 deg C to room temperature, 2) room temperature, 8 h View Scheme

2: NaBH4 / methanol / Ambient temperature 3: toluene-p-sulfonic acid / toluene / 4 h / Heating 4: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -78 deg C to room temperature, 2) room temperature, 8 h View Scheme

1: 1) NaH / 1) toluene, reflux, 30 min, 2) reflux, 1 h 2: 51.4 percent / NaBH4 / ethanol / 6 h 4: NaBH4 / methanol / Ambient temperature 5: toluene-p-sulfonic acid / toluene / 4 h / Heating 6: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -78 deg C to room temperature, 2) room temperature, 8 h View Scheme

triethylamine; 4-(N,N-dimethlyamino)pyridine T=20°C; 3 h;

1: 91.3 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 1) -30 deg C, 3 h, 2) room temperature, 1 h 2: 44.7 percent / m-chloroperbenzoic acid / CH2Cl2 / 1) 0 deg C, 1 h, 2) room temperature, 12 h 3: 33 percent / Bu3SnH, azoisobutyronitrile / benzene / 15 h / Heating View Scheme