Triethylamine → (-)-2-[2-(4-Chlorophenyl)benzyl]sulphinylacetamide

Participants

Reaction Conditions

Reaction Steps

A solution of (S,S)-(−)-diethyl-tartrate (2.47 g; 0.012 mol; 0.4 eq.) in a solvent (3.5 vol. vs thioacetamide) was introduced in a reactor with an impeller, containing 6.5 vol (vs thioacetamide) of the same solvent. The solution was stirred and heated to 50° C. before adding 0.2 equivalent of titanium (IV) tetraisopropoxide (1.71 g; 1.77 mL; 0.006 mol; 0.2 eq) and water (QSP to achieve 0.095 eq. in the mixture) and kept stirring at 50° C. for one hour. In these conditions, the resulting chiral titanium complex had the stoichiometry of DET/Ti(OiPr)4/H2O: 2/1/0.475 and corresponded to 0.2 eq. with respect to the thioacetamide. After stirring at 50° C. for one hour, 1.0 eq. (8.75 g; 0.03 mol) of 2-[2-(4-chlorophenyl)benzyl]sulphanyl acetamide was added and contacted for 30 min. After cooling to 20° C., were successively added 0.2 eq. (0.61 g; 0.84 mL; 0.006 mol) of triethylamine and around 10 minutes later, 1.0 eq (4.57 g; 5.0 mL; 0.03 mol) of cumene hydroperoxide within less than 5 minutes.

Provenance & Evidence