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Magnesium Catalysis Mediated Tetrazoles in Desymmetrization Reaction of Aziridines.

Organic letters (2017-05-31)
Dan Li, Kezhou Wang, Linqing Wang, Yuan Wang, Pengxin Wang, Xin Liu, Dongxu Yang, Rui Wang
ABSTRAKT

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.

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Sigma-Aldrich
Di-n-butylmagnesium solution, 1.0 M in heptane