Enantioselective Ring Opening of meso-Aziridines with TMS-Protected Thiophenol

Significance

The authors report an organocatalytic desymmetrization of meso-aziridines 1 via ring opening with (phenylthio)trimethylsilane (2) to give the corresponding acylaminothioethers 4 in good yields and enantiomeric ratios up to 99.5:0.5. The catalytically active species, a chiral Lewis acid, is formed in situ from the reaction of the chiral phosphoric acid 3 with silylthioether 2.