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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
Approach Toward Stereoselective α-Arylation by Pd/Cu-Catalyzed Arylboration of Electron Deficient Alkenes
Suman Das1, Maeve A Reilly1, Stanna K Dorn1
1Department of Chemistry, Indiana University, 800 E. Kirkwood Ave, Bloomington, 47401, Indiana.
Abstract:
Palladium-catalyzed cross coupling of enolates-α-arylation-is an established method for chemical synthesis. A major challenge in the field is control of stereochemistry for the α-carbon. This is typically due to facile epimerization under the basic reaction conditions for α-arylation. In this study, an alternative approach is presented that involves the Pd/Cu-catalyzed arylboration of electron deficient alkenes. The products are generated with high levels of diastereoselectivity for a broad range of substitution patterns. Enantioselective variants are also presented in addition to product derivatizations.
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