The catalytic tandem oxidation/benzilic ester rearrangement (BER): insights into reaction mechanism and stereoselectivity |
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Authors: | Carolina Silva Marques,Anthony J. Burke,Olí via R. Furtado |
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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 |
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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. |
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Keywords: | Benzilic acid rearrangment Benzilic ester rearrangment Isotopic label Regioselectivity Diastereoselectivity |
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