Magnesium Catalysis Mediated Tetrazoles in Desymmetrization Reaction of Aziridines

Org Lett. 2017 Jun 16;19(12):3211-3214. doi: 10.1021/acs.orglett.7b01333. Epub 2017 May 30.

Abstract

A magnesium-catalyzed asymmetric ring-opening reaction of aziridines with substituted tetrazoles is reported. The current protocol proceeds smoothly and gives the corresponding desymmetrization products in high yields and good enantioselectivities. A new chiral ligand was synthesized from azetidine and (R)-BINOL and was employed in the current in situ generated magnesium catalyst. The Mg(II)-mediated desymmetrization reaction could be performed on gram scale under mild conditions and was transformed to chiral alkyl amines by a deprotection process.

Publication types

  • Research Support, Non-U.S. Gov't