in tetrahydrofuran T=-78°C; Grignard reaction; allylation;

1.1: OsO4 1.2: 80 percent / NaIO4 2.1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C 3.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 4.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 5.1: 80 percent / PCC 6.1: LDA 7.1: 88 percent / CSA / methanol 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: 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: 68 percent / tetrahydrofuran / -78 - 20 °C 6.1: Hg(OAc)2; water / tetrahydrofuran / 2.5 h 6.2: 60 percent / tetrabutylammonium iodide / tetrahydrofuran; H2O / 2 h 7.1: 100 percent / HF-pyridine / tetrahydrofuran / 12 h / 20 °C 8.1: 96 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 9.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation 9.2: 37 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C 10.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C 11.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 11.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h 12.1: 92 percent / HF*pyridine / tetrahydrofuran 13.1: 97 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: 68 percent / tetrahydrofuran / -78 - 20 °C 6.1: Hg(OAc)2; water / tetrahydrofuran / 2.5 h 6.2: 60 percent / tetrabutylammonium iodide / tetrahydrofuran; H2O / 2 h 7.1: 100 percent / HF-pyridine / tetrahydrofuran / 12 h / 20 °C 8.1: 96 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 9.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation 9.2: 37 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C 10.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C 11.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 11.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h 12.1: 92 percent / HF*pyridine / tetrahydrofuran View Scheme

in benzene Heating;

PBS buffer; aldolase antibody 84G3 T=37°C; pH=7.4; 120 h;

sodium hydroxide in ethanol; water

1: 57 percent / DIBAL-H 2: 89 percent View Scheme

(polystyrylmethyl)trimethylammonium perruthenate; oxygen in toluene 16 h; Heating;