Synthesis 2015; 47(17): 2570-2577
DOI: 10.1055/s-0034-1378813
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© Georg Thieme Verlag Stuttgart · New York

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

Marie S. T. Morin
a  Ecole Nationale Supérieure de Chimie de Rennes, CNRS UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708, Rennes Cedex 7, France   Email: marc.mauduit@ensc-rennes.fr
,
Thomas Vives
a  Ecole Nationale Supérieure de Chimie de Rennes, CNRS UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708, Rennes Cedex 7, France   Email: marc.mauduit@ensc-rennes.fr
,
Olivier Baslé
a  Ecole Nationale Supérieure de Chimie de Rennes, CNRS UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708, Rennes Cedex 7, France   Email: marc.mauduit@ensc-rennes.fr
,
Christophe Crévisy*
a  Ecole Nationale Supérieure de Chimie de Rennes, CNRS UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708, Rennes Cedex 7, France   Email: marc.mauduit@ensc-rennes.fr
,
Virginie Ratovelomanana-Vidal*
b  PSL Research University, Chimie ParisTech-CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France
,
Marc Mauduit*
a  Ecole Nationale Supérieure de Chimie de Rennes, CNRS UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708, Rennes Cedex 7, France   Email: marc.mauduit@ensc-rennes.fr
› Author Affiliations
Further Information

Publication History

Received: 06 May 2015

Accepted after revision: 29 June 2015

Publication Date:
03 August 2015 (eFirst)

Abstract

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 asymmetric conjugate addition 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.

Supporting Information

 
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