Oxonereg;; 1,1,1-trifluoropropanone; (ethylenedinitrilo)tetraacetic acid disodium salt; sodium hydrogencarbonate in water; acetonitrile T=0°C;

Oxonereg;; 1,1,1-trifluoropropanone; (ethylenedinitrilo)tetraacetic acid disodium salt; sodium hydrogencarbonate in water; acetonitrile T=0°C;

1.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 2.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation 2.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C 3.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C 4.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 4.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h 5.1: 99 percent / HF*pyridine / tetrahydrofuran 6.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C View Scheme

1.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation 1.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C 2.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C 3.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 3.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h 4.1: 99 percent / HF*pyridine / tetrahydrofuran 5.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C View Scheme

1.1: tributylphosphine oxide / diethylaluminum chloride; R(a)-[2,2'-dihydroxy-3,3'-bis(CH2Ph2PO)]-1,1'-binaphthyl / CH2Cl2; hexane / 0.5 h / -40 °C 1.2: CH2Cl2; hexane / 39 h 1.3: 97 percent / trifluoroacetic acid / CH2Cl2; hexane / 1 h / 20 °C 2.1: 83 percent / aq. HCl / 5 h / 90 °C 3.1: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C 4.1: 94 percent / DIBAL / toluene / 1 h / -78 °C 5.1: tetrahydrofuran; hexane / 0.67 h / -78 °C 5.2: 79 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 51 percent / ammonium formate; tributylphosphine / Pd(OAc)2 / benzene / 24 h / 50 °C 7.1: 26 percent / Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1 h / -50 °C 8.1: 59 percent / I2 / CH2Cl2 / 12 h / 20 °C 9.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 10.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation 10.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C 11.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C 12.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 12.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h 13.1: 99 percent / HF*pyridine / tetrahydrofuran 14.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C View Scheme

1.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C 1.2: 87 percent / tetrahydrofuran / -78 - 20 °C 2.1: SmI2 / tetrahydrofuran / 0.33 h / 0 °C 3.1: 114 mg / H2O; B(OH)3 / tetrahydrofuran / 0.5 h / 20 °C 4.1: 91 percent / Et3B; NaBH4 / methanol; tetrahydrofuran / 17 h / -78 °C 5.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 6.1: 58 mg / Bu4NF*3H2O / tetrahydrofuran / 6 h / Heating 7.1: 79 percent / Et3N; DMAP / CH2Cl2 / 15 h / 20 °C 8.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 9.1: 4.4 mg / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 10.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 11.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 12.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 13.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 14.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 15.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 16.1: 2,4,6-trichlorobenzoyl chloride; Et3N 16.2: 74 percent / 4-dimethylaminopyridine 17.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 18.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: DIBAL-H / CH2Cl2 / 5.5 h / -78 °C 2.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C 2.2: 87 percent / tetrahydrofuran / -78 - 20 °C 3.1: SmI2 / tetrahydrofuran / 0.33 h / 0 °C 4.1: 114 mg / H2O; B(OH)3 / tetrahydrofuran / 0.5 h / 20 °C 5.1: 91 percent / Et3B; NaBH4 / methanol; tetrahydrofuran / 17 h / -78 °C 6.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 7.1: 58 mg / Bu4NF*3H2O / tetrahydrofuran / 6 h / Heating 8.1: 79 percent / Et3N; DMAP / CH2Cl2 / 15 h / 20 °C 9.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 10.1: 4.4 mg / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 11.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 12.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 13.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 14.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 15.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 16.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 17.1: 2,4,6-trichlorobenzoyl chloride; Et3N 17.2: 74 percent / 4-dimethylaminopyridine 18.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 19.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 96 percent / 4-DMAP; Et3N / CH2Cl2 / 2 h 2.1: N-methylmorpholine N-oxide; water / OsO4 / acetone; butan-1-ol / 2 h / 0 °C 3.1: NaIO4 / tetrahydrofuran; H2O / 1.25 h / 20 °C 4.1: 0.014 g / HMPA / tetrahydrofuran / 0.5 h / -78 - 20 °C 5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 5.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 6.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 7.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 8.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 9.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 10.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 11.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C 12.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2 h / -50 - -30 °C View Scheme

1: 1) LDA / 1) THF, -78 deg C, 15 min; -30 deg C, 1.5 h, 2) THF, -78 deg C, 15 min; -40 deg C, 1 h 2: 0.940 g / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h 3: 46 percent / RuCl2(=CHPh)(PCy3)2 / CH2Cl2 / 20 h / 25 °C 4: 90 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C 5: 62 percent / Na2EDTA, 1,1,1-trifluoroacetone, Oxone, NaHCO3 / acetonitrile; H2O / 0 °C View Scheme

1: 1) LDA / 1) THF, -78 deg C, 15 min; -30 deg C, 1.5 h, 2) THF, -78 deg C, 15 min; -40 deg C, 1 h 2: 0.940 g / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h 3: 46 percent / RuCl2(=CHPh)(PCy3)2 / CH2Cl2 / 20 h / 25 °C 4: 90 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C 5: 62 percent / Na2EDTA, 1,1,1-trifluoroacetone, Oxone, NaHCO3 / acetonitrile; H2O / 0 °C View Scheme