Catalytic Enantioselective γ‐Selective Additions of 2‐Allylazaarenes to Activated Ketones. (27th February 2017)

• Record Type: Journal Article
• Authors: Bai, Xiangbin; Zeng, Guangkuo; Shao, Tianju; Jiang, Zhiyong
• Is Part Of: Angewandte Chemie. Volume 129:Number 13(2017)
• Page Start: 3738
• Page End: 3742
• Publication Date: 2017-02-27
• Subjects: Allylverbindungen -- Arene -- Heterocyclen -- Organokatalyse -- Synthesemethoden; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201700190
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Reported herein is the first example of 2‐allylazaarenes in asymmetric catalysis. Highly γ‐selective allylation was demonstrated for activated ketones, including isatins and trifluoromethyl ketones. In the presence of either an amino‐acid‐based tertiary amine or quaternary ammonium salt catalyst, two series of tertiary hydroxy‐containing moieties were installed at the remote δ‐position of azaarenes in good chemical yields, excellent enantioselectivities, and E / Z ratios. The success of current γ‐selective reactions should provide inspiration for expansion to other allylazaarene derivatives and would open up new paradigms for the synthesis of chiral γ‐ and/or δ‐functionalized azaarenes. Abstract : Fernwirkung : Die hohe γ‐Selektivität von 2‐Allylazaarenen bestimmt ihre Allylierungsreaktionen mit aktivierten Ketonen, einschließlich Isatinen und Trifluormethylketonen. In Gegenwart eines Aminosäure‐basierten tertiären Amins oder quartären Ammoniumsalzes wurden zwei Arten von tertiären Hydroxyeinheiten in δ‐Stellung eingeführt.