perfluorodecahydronaphthalene in hexane; toluene 1 h; Heating;

in pyridine T=20°C; 20 h;

manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; (R,R)-Ph-BOX in α,α,α-trifluorotoluene T=120°C; 24 h; Molecular sieveInert atmosphereSealed tube; optical yield given as percent eeenantioselective reaction;

1: pyridine / dichloromethane / 20 °C / |Sealed tube; |Inert atmosphere 2: copper diacetate; potassium hydrogencarbonate; manganese(IV) oxide / toluene / 24 h / 135 °C / |Sealed tube; |Inert atmosphere View Scheme

1: boron trifluoride diethyl etherate / xylenes / 6 h / 180 °C 2: pyridine / dichloromethane / 24 h / 20 °C 3: manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; (R,R)-Ph-BOX / α,α,α-trifluorotoluene / 24 h / 120 °C / Molecular sieve; Inert atmosphere; Sealed tube View Scheme

1: pyridine / dichloromethane / 24 h / 20 °C 2: manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; (R,R)-Ph-BOX / α,α,α-trifluorotoluene / 24 h / 120 °C / Molecular sieve; Inert atmosphere; Sealed tube View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C 2: boron trifluoride diethyl etherate / xylenes / 6 h / 180 °C 3: pyridine / dichloromethane / 24 h / 20 °C 4: manganese(IV) oxide; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; (R,R)-Ph-BOX / α,α,α-trifluorotoluene / 24 h / 120 °C / Molecular sieve; Inert atmosphere; Sealed tube View Scheme