Quinox, a Quinoline-Type N-Oxide, as Organocatalyst in the Asymmetric Allylation of Aromatic Aldehydes with Allyltrichlorosilanes: The Role of Arene–Arene Interactions†
Andrei V. Malkov Dr.
Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK, Fax: (+44) 141-33-488
Search for more papers by this authorLenka Dufková
Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK, Fax: (+44) 141-33-488
Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
Search for more papers by this authorLouis Farrugia Dr.
Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK, Fax: (+44) 141-33-488
Search for more papers by this authorPavel Kočovský Prof. Dr.
Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK, Fax: (+44) 141-33-488
Search for more papers by this authorAndrei V. Malkov Dr.
Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK, Fax: (+44) 141-33-488
Search for more papers by this authorLenka Dufková
Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK, Fax: (+44) 141-33-488
Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
Search for more papers by this authorLouis Farrugia Dr.
Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK, Fax: (+44) 141-33-488
Search for more papers by this authorPavel Kočovský Prof. Dr.
Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK, Fax: (+44) 141-33-488
Search for more papers by this authorWe thank the University of Glasgow, the Socrates Exchange program, and Dr. Alfred Bader for financial support.
Graphical Abstract
Die Allylierung aromatischer Aldehyde mit Allyltrichlorsilanen kann durch die neue Lewis-Base quinox organisch katalysiert werden. Bei elektronenarmen Aldehyden werden hohe Enantioselektivitäten beobachtet, bei elektronenreichen dagegen nur geringe (siehe Schema). Dies deutet darauf hin, dass die Aren-Aren-Wechselwirkung zwischen dem elektronenreichen Katalysator und dem angreifenden Aldehyd die enantiofaciale Selektivität bestimmt.
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