Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 15, Pages 10630-10639Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01300
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- University of Salerno
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A highly stereoselective access to 3-sulfinyl-substituted isoindolinones has been achieved by a tandem organocatalytic addition/cyclization reaction, followed by diastereoselective oxidation with MCPBA. Enantioenriched isoindolinone N,S-acetals were obtained through a dynamic kinetic asymmetric transformation induced by a bifunctional chiral thiourea organocatalyst, leading to high diastereocontrol in the subsequent sulfoxidation. Theoretical rationale for the stereoselectivity of the oxidation reaction is provided through DFT calculations.
A highly stereoselective access to 3-sulfinyl-substituted isoindolinones has been achieved by a tandem organocatalytic addition/cyclization reaction of 2-carbobenzyloxy-N-tosylbenzylidenimine with thiols and succeeding diastereoselective oxidation with MCPBA. First, enantioenriched isoindolinone N,S-acetals have been obtained through a dynamic kinetic asymmetric transformation induced by a bifunctional chiral thiourea organocatalyst. In turn, the newly created carbon stereocenter enabled a high diastereocontrol in the subsequent sulfoxidation. Based on DFT calculations, a theoretical rationale for the stereoselectivity of the oxidation reaction is also provided.
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