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The catalytic tandem oxidation/benzilic ester rearrangement (BER): insights into reaction mechanism and stereoselectivity
Authors:Carolina Silva Marques,Anthony J. Burke,Olí  via R. Furtado
Affiliation:a Departamento de Química and Centro de Química de Évora, Universidade de Évora, Rua Romão Romalho 59, 7000 Évora, Portugal
b Departamento de Tecnologia de Indústrias Químicas, Instituto Nacional de Engenharia, Tecnologia e Inovação, Estrada do Paço do Lumiar, Edifício F, 1649-038 Lisboa, Portugal
Abstract:This Letter describes an expeditious regiospecific and stereoselective approach to tertiary α-hydroxyesters via a simple one pot tandem catalytic oxidation/benzilic ester rearrangement of acyclic α-hydroxyketone substrates. Mechanistic studies confirming the regioselective nature of this reaction are discussed, including some insights into the nature of the stereoselectivity encountered in this reaction.
Keywords:Benzilic acid rearrangment   Benzilic ester rearrangment   Isotopic label   Regioselectivity   Diastereoselectivity
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