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Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2021

Gold-Catalyzed Carboamination of Allenes by Tertiary Amines Proceeding with Benzylic Group Migration

Résumé

Tertiary amines bearing a benzyl-type group (CH2Ar) undergo Au(I)-catalyzed intramolecular addition to allenes. A formal 1,3-transfer of the CH2Ar group takes place during the cyclization. As demonstrated by both experimental and DFT studies, these unprecedented intramolecular carboaminations involve two consecutive [3,3] rearrangements via a dearomatized intermediate. Because of the poor stability of the enamine products, protocols were developed to convert them in situ to more stable polycyclic chiral compounds.
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Dates et versions

hal-03267804 , version 1 (22-06-2021)

Identifiants

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Pierre Milcendeau, Vincent Gandon, Xavier Guinchard. Gold-Catalyzed Carboamination of Allenes by Tertiary Amines Proceeding with Benzylic Group Migration. Advanced Synthesis and Catalysis, 2021, 363 (11), pp.2893-2902. ⟨10.1002/adsc.202100007⟩. ⟨hal-03267804⟩
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