Synthesis of Chiral Vicinal Amino Alcohol Derivatives via Lewis Acid‐Catalyzed Asymmetric Ring Opening of Aziridines with Alcohols and Carboxylic Acids

Author:

Ma Chen‐Xue1,Hu Qi1,Qin Hai‐Lin1,Yang Gaosheng1,Chai Zhuo1ORCID

Affiliation:

1. MOE Key Laboratory of Functionalized Molecular Solids Anhui Key Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base) College of Chemistry and Materials Science Anhui Normal University 189 South Jiuhua Road Wuhu Anhui 241002 People's Republic of China

Abstract

AbstractUnder the catalysis of a Cu(I) or Ag(I) salt with a chiral diphosphine ligand, the enantioselective nucleophilic ring opening of racemic 2‐styrenylaziridines via kinetic resolution or dynamic kinetic asymmetric transformation (DyKAT) and of meso aziridines via desymmetrization with alcohols was realized. The reaction provided a range of chiral vicinal amino ether derivatives in 47%‐98% yields and with 50%–98% ee. The reaction could be extended to aliphatic carboxylic acids as nucleophiles. The synthetic utility was demonstrated in a four‐step formal synthesis of a diastereomer of the antirythmetic agent vernakalant.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Anhui Province

Publisher

Wiley

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