Palladium/,'-Disulfonyl Bisimidazoline-Catalyzed Enantioselective Addition of Arylboronic Acids to Cyclic -Sulfonyl Ketimines.

J Org Chem

School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.

Published: November 2020

AI Article Synopsis

  • * This reaction leads to the synthesis of three types of chiral quaternary carbon-containing sultams, achieving high yields and excellent enantioselectivity (over 99% ee).
  • * The catalytic process is notably robust, showing a high tolerance to oxygen, making it a simple and effective method for creating enantioenriched cyclic quaternary stereocenters.

Article Abstract

The combination of Pd(TFA) and an ,'-disulfonyl bisimidazoline ligand shows high catalytic activity and excellent asymmetric induction in the addition of arylboronic acids to cyclic -sulfonyl ketimines including benzo[]isothiazole-1,1-dioxides, benzo[][1,2,3]oxathiazine-2,2-dioxides, and 1,2,5-thiadiazole-1,1-dioxides, by which three types of chiral quaternary carbon-containing sultams with substantial substitution diversity were synthesized with high yields and excellent enantioselectivities (up to >99% ee). The current catalysis demonstrated a remarkable tolerance to oxygen and thus provided an operationally simple approach for constructing enantioenriched cyclic quaternary stereocenters.

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Source
http://dx.doi.org/10.1021/acs.joc.0c01722DOI Listing

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