X-Ray absolute configuration and circular dichroic properties of a chiral oxaziridine containing two phenyl chromophores in a trans configuration. Application of the circular dichroism exciton chirality method to the optical activity of (S,S)–(-)-3-phenyl-2-phenylsulphonyloxaziridine

Abstract

Bijvoet X-ray diffraction analysis of crystalline, optically pure 3-phenyl-2-phenylsulphonyloxaziridine (–)-(2), obtained by asymmetric oxidation of the corresponding prochiral N-benzylidenephenyl-sulphonylimine (1) with (1S)-(+)-peroxycamphoric acid, followed by fractional crystallization of the crude reaction product, shows that the absolute configuration at the chiral nitrogen and carbon atoms of the oxaziridine ring is (2S,3S). Absolute configuration of (2) was also determined independently by application of the circular dichroism exciton chirality method.