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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Iridium-Catalyzed Enantioselective N-Allylation of Aminoquinones with Racemic Allylic Alcohols
1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry, Nanjing University, Nanjing, Jiangsu210023, China.
Abstract:
An iridium-catalyzed enantioselective N-allylation of aminoquinones with racemic allylic alcohols has been developed, affording chiral aminoquinone derivatives in excellent yields (up to 96%) and with high enantioselectivities (up to 99% ee). The reaction exhibits a broad substrate scope, encompassing aryl-, alkyl-, and heterocyclic-substituted allylic alcohols as well as a diverse range of aminoquinones. The observed chemoselectivity in this asymmetric allylation is proposed to arise from tautomerization of the aminoquinone, which makes nitrogen rather than carbon the nucleophilic site.
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