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Ytterbium Triflate-Promoted Tandem One-Pot Oxidation-Cannizzaro Reaction of Aryl Methyl Ketones

Massimo Curini,* Francesco Epifano, Salvatore Genovese, M. Carla Marcotullio and Ornelio Rosati

*Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Via del Liceo, 06123 Perugia, Italy, Email: curmaxunipg.it

M. Curini, F. Epifano, S. Genovese, M. C. Marcotullio, O. Rosati, Org. Lett., 2005, 7, 1331-1333.

DOI: 10.1021/ol050125e (free Supporting Information)


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Abstract

Ytterbium triflate is an effective catalyst for the synthesis of either isopropyl esters or free α-hydroxy-arylacetic acids (mandelic acid derivatives) from substituted aromatic glyoxals and aryl methyl ketones, respectively. The environmentally friendly synthesis of mandelic acid derivatives provides products in excellent yield without any further purification after the usual workup.

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Key Words

Cannizzaro Reaction, Mandelic Acid Derivatives, Selenium Dioxide


ID: J54-Y2005-330