NSC122659 synthesis

Yield:9 % ee

Reaction Conditions:

with μ-Oxido-bis({S(+)-2-[(1-oxidopropyl)iminomethyl]-4-methoxyphenolato-κ³N,O,O'}oxidovanadium(V));dihydrogen peroxide in methanol;dichloromethane at 20; for 0.5 h;Catalytic behavior;Overall yield = 91 %;Reagent/catalyst;

Steps:

Catalytic activity

General procedure: In typical procedure, to a solution of vanadium(V) complex (0.010 mmol) in 3 ml of CH2Cl2/MeOH solution (7:3, v/v), sulfide (1.00 mmol) was added at room temperature or -20 °C, together with 1,3,5-trimethoxybenzene as internal standard. Hydrogen peroxide (30% aqueous) or cumene hydroperoxide (CHP) as oxidants were added (1.10 mmol) by small portions and the resulting mixture was stirred. After the appropriate reaction time, the solution was quenched with 2 ml of sodium sulfite solution (0.1 M) and extracted with CH2Cl2 (3 × 5 ml). The combined organic layers were evaporated to dryness. The solid product dissolved in CDCl3 was analyzed (yield and ee value) by 1H NMR spectra in the presence of chiral shift reagent Eu(hfc)3 (where Hhfc is 3-(heptafluoropropylhydroxymethylene)-(+)-camphoric acid) [23].

References:

Romanowski, Grzegorz;Lis, Tadeusz [Inorganica Chimica Acta,2013,vol. 394,p. 627 - 634]