2,3‐Bifunctionalized Aziridines: Regioselective MgBr₂‐Mediated Opening Under “Chelation Controlled” Conditions

Abstract

The results obtained in the MgBr₂‐mediated opening of 2,3‐bifunctionalised aziridines are reported. The study shows that, at least for the Z stereoisomers, the bromide attacks the aziridine ring in the α position to all functional groups considered with high regioselectivity, thus suggesting a strong aptitude for MgBr₂ to coordinate a benzyloxy function.

Keywords:

• 2,3‐Bifuctionalized aziridines
• MgBr₂
• Chelation control

Notes

^aCompounds 10, 11a and 11b were obtained as single diastereoisomers. Since the diastereocontrol of the Grignard addition was not our aim, we did not investigate its stereochemistry.