1.1: MeLi*LiBr / diethyl ether / 0.5 h / 20 °C 1.2: 85 percent / (1S,2R)-2-(p-tolylsulfinyl)-1-trifluoromethylethanol / diethyl ether; CH2Cl2 / 1.5 h / -78 °C 2.1: 87 percent / Na; naphthalene; acetamide / tetrahydrofuran / -78 °C View Scheme

1: With methyllithium; lithium bromide Metallation; 2: With chiral α-sulfinyl alcohol T=-50°C; protonation;

1: (i) MeLi, THF, (ii) /BRN= 2047179/, Br2 2: aq. H2O2, Py / CH2Cl2 View Scheme