Cooperative Heterobimetallic Zinc/Alkaline Earth Metal Catalysis: A Zn/Sr Aminophenol Sulfonamide Complex for Catalytic Asymmetric Michael Addition of 3-Acetoxy-2-oxindoles to β-Ester Enones.

J Org Chem

Chongqing Research Center for Pharmaceutical Engineering, Research Center for Innovative Pharmaceutical and Excipient Analysis Technology, College of Pharmacy, Chongqing Medical University, Chongqing 400016, China.

Published: May 2021

AI Article Synopsis

  • A new zinc/strontium catalyst has been created for efficiently facilitating the asymmetric Michael addition reaction involving 3-acetoxy-2-oxindoles and β-ester enones.
  • The reaction achieves high yields along with excellent enantioselectivities and diastereoselectivities.
  • This method highlights the potential of 3-acetoxy-2-oxindoles as a stable precursor for producing chiral 3-substituted 3-hydroxy-2-oxindoles.

Article Abstract

A heterobimetallic zinc/strontium catalyst has been developed for the asymmetric Michael addition of 3-acetoxy-2-oxindoles to β-ester enones in high yields with excellent enantioselectivities and high diastereoselectivities. This process represents that 3-acetoxy-2-oxindoles can be used as a stable air- and base-tolerant precursor for chiral 3-substituted 3-hydroxy-2-oxindoles.

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http://dx.doi.org/10.1021/acs.joc.1c00379DOI Listing

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