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Cu-Catalyzed -Arylation of Prolinamides: Access to Enantioenriched DMAP Analogues and Its Application in Black Rearrangement. | LitMetric

Cu-Catalyzed -Arylation of Prolinamides: Access to Enantioenriched DMAP Analogues and Its Application in Black Rearrangement.

J Org Chem

NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

Published: January 2023

AI Article Synopsis

  • * This process facilitated the creation of chiral 3-amino DMAP catalysts.
  • * The resulting enantioenriched DMAP was effectively utilized in an asymmetric reaction, producing 3,3-disubstituted benzofuran-2-ones with a yield of up to 96% and an enantiomeric excess (ee) of 97%.

Article Abstract

A CuI-catalyzed C-N coupling reaction of 3-bromo-DMAP with l-prolinamides was conducted at 80 °C in 12-16 h, where the prolinamide's structure had an accelerating effect on the Ullmann-type reaction. This reaction was used to construct chiral 3-amino DMAP catalysts. Furthermore, enantioenriched DMAP analogue was applied in an asymmetric Black rearrangement of 2-benzofuranylcarbonates, affording 3,3-disubstituted benzofuran-2-ones in up to 96% yield and 97% ee.

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Source
http://dx.doi.org/10.1021/acs.joc.2c02368DOI Listing

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