tetrachloromethane; tributylphosphine 0.5 h; Reflux;

3-chloro-benzenecarboperoxoic acid in pyridine; dichloromethane 1.) -70 degC 2 h, 2.) R.T. overnight;

1: CH2Cl2 / 0.17 h / -70 °C 2: 50 percent / m-chloroperbenzoic acid / CH2Cl2; pyridine / 1.) -70 degC 2 h, 2.) R.T. overnight View Scheme

1: LiAlH4 / diethyl ether 2: CCl4, trioctylphosphane / 0.5 h View Scheme

1: lithium aluminium tetrahydride / diethyl ether / -78 - 0 °C 2: thionyl chloride / dichloromethane / 3 h / 0 - 20 °C / |Inert atmosphere View Scheme

potassium carbonate in N,N-dimethyl-formamide 15 h; Ambient temperature;

O,O'-(S)-(1,1'-dinaphthyl-2,2'-diyl)-N,N-di-(S,S)-[2-phenylethylphosphoramidite]; copper(I) thiophene-2-carboxylate in diethyl ether; dichloromethane T=-78°C;

1: 1-chloromethylcyclopentene With O,O'-(S)-(1,1'-dinaphthyl-2,2'-diyl)-N,N-di-(S,S)-[2-phenylethylphosphoramidite]; copper(I) thiophene-2-carboxylate in dichloromethane T=20°C; Inert atmosphere; 2: n-butyl-magnesium chloride in diethyl ether; dichloromethane T=-78°C; 5 h; Inert atmosphere; optical yield given as percent ee;

1: 1-chloromethylcyclopentene With copper(I) thiophene-2-carboxylate; O,O'-((S)-1,1'-dinaphthyl-2,2'-diyl)-N,N'-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite in dichloromethane T=20°C; Inert atmosphere; 2: n-butyl-magnesium chloride in diethyl ether; dichloromethane T=-78°C; 5 h; Inert atmosphere; optical yield given as percent ee;

1: (i) NaOMe, MeOH, (ii) /BRN= 1850241/, (iii) aq. NaOH 2: NaH / diethyl ether / Heating 3: (i) NaH, dioxane, (ii) /BRN= 741886/ View Scheme