Efficiency of Industrially Relevant Atropisomeric Diphosphines in Copper-Catalyzed 1,4-Asymmetric Conjugate Addition of Dialkylzincs to Cyclic or Acyclic Enones or Dienones - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2015

Efficiency of Industrially Relevant Atropisomeric Diphosphines in Copper-Catalyzed 1,4-Asymmetric Conjugate Addition of Dialkylzincs to Cyclic or Acyclic Enones or Dienones

Résumé

Industrially relevant atropisomeric diphosphines such as 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP), 6,6'-bis(diphenylphosphino)-2,2',3,3'-tetrahydro-5,5'-bi-1,4-benzodioxin (SYNPHOS), and 5,5'-bis(diphenylphosphino)-2,2,2',2'-tetrafluoro-4,4'-bi-1,3-benzodioxole (DIFLUORPHOS) have demonstrated their efficiency in the copper-catalyzed asym. conjugate addn. of various dialkylzincs to α-aryl enones, α-aryl dienones, and cyclic dienones. Excellent 1,4- or 1,6-regioselectivities and enantioselectivities (up to 97% ee) were attained, even with challenging sterically hindered Michael acceptors.
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Dates et versions

hal-01188236 , version 1 (19-10-2015)

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Marie S. T. Morin, Thomas Vives, Olivier Baslé, Christophe Crévisy, Virginie Ratovelomanana-Vidal, et al.. Efficiency of Industrially Relevant Atropisomeric Diphosphines in Copper-Catalyzed 1,4-Asymmetric Conjugate Addition of Dialkylzincs to Cyclic or Acyclic Enones or Dienones. Synthesis: Journal of Synthetic Organic Chemistry, 2015, 47 (17), pp.2570--2577. ⟨10.1055/s-0034-1378813⟩. ⟨hal-01188236⟩
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