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Uniting C1-Ammonium Enolates and Transition Metal Electrophiles via Cooperative Catalysis: The Direct Asymmetric α-Allylation of Aryl Acetic Acid Esters

Kevin J. Schwarz, Jessica L. Amos, J. Cullen Klein, Dung T. Do and Thomas N. Snaddon*

*Department of Chemistry, Indiana University, 800 E. Kirkwood Ave., Bloomington, Indiana 47405, United States, Email: tsnaddonindiana.edu

K. J. Schwarz, J. L. Amos, J. C. Klein, D. T. Do, T. N. Snaddon, J. Am. Chem. Soc., 2016, 138, 5214-5217.

DOI: 10.1021/jacs.6b01694


Abstract

Cooperative catalysis facilitates the direct asymmetric α-allylation of readily available aryl acetic acid esters. Since enantioselection is determined by a chiral nucleophile, this conceptual approach to cooperative catalysis constitutes a potentially general solution to the direct catalytic asymmetric α-functionalization of acyclic esters.

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Postulated Cooperative Catalysis Mechanism



Key Words

allylation


ID: J48-Y2016