(2S)-2-[(2S*,5R*,6R*)-5,6-Dimeth-oxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethyl-ethylsulfon-yl]aziridine

Acta Crystallogr Sect E Struct Rep Online. 2010 Nov 27;66(Pt 12):o3335. doi: 10.1107/S1600536810048816.

Abstract

The reaction of a sulfur ylide with a chiral non-racemic sulfinyl imine afforded the desired aziridine in excellent yield and subsequent oxidation of the sulfinyl moiety dissolved in anhydrous dichloro-methane using a 75% aqueous solution of 3-chloro-per-oxy-benzoic acid afforded the title compound, C(14)H(27)NO(6)S. The configuration of the newly formed stereogenic center at the point of attachment of the 1,4-dioxane ring to the aziridine ring is S. The configurations of the pre-existing sites 2-, 5-, and 6-positions of the 1,4-dioxane ring prior to reaction of sulfinyl imine with the sulfur ylide are S, R, and R, respectively. The C-N bond lengths of the aziridine are 1.478 (2) and 1.486 (2) Å.