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Desymmetrization of Cyclohexadienones through Phase-Transfer-Catalyzed Stereoselective Intramolecular Aza-Michael Addition with Chiral Sulfinamide Nucleophiles. | LitMetric

AI Article Synopsis

  • The paper discusses a method for desymmetrizing cyclohexadienones using a stereoselective intramolecular reaction involving a chiral sulfinamide nucleophile.
  • The process uses phase-transfer catalysis to enhance the reaction efficiency.
  • The reaction achieved high yields of nitrogen-containing bicyclic compounds, with yields up to 93% and a diastereomeric ratio exceeding 20:1.

Article Abstract

This paper reports the desymmetrization of cyclohexadienones through stereoselective intramolecular aza-Michael addition with a tethered chiral sulfinamide nucleophile. The reaction was facilitated by phase-transfer catalysis and produced various nitrogen-containing bicyclic compounds with a yield of up to 93% and a diastereomeric ratio of up to >20:1.

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Source
http://dx.doi.org/10.1021/acs.joc.3c01253DOI Listing

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