(2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine

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 dichloromethane using a 75% aqueous solution of 3-chloroperoxybenzoic acid afforded the title compound, C14H27NO6S. 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.