Original synthesis of oxiranes via TDAE methodology: reaction of 2,2-dibromomethylquinoxaline with aromatic aldehydes

We report herein the reaction of 2,2-dibromomethylquinoxaline 2 with aromatic aldehydes 3a-g in the presence of TDAE. These reactions lead to a mixture of cis/trans-isomers of corresponding oxiranes 4a-g in good yields. The stereoselectivity of the reaction was sensitive to steric hindrance.

We report herein the reaction of 2,2-dibromomethylquinoxaline with aromatic aldehydes in the presence of TDAE. These reactions lead to a mixture of cis/trans-isomers of corresponding oxiranes.