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Synthesis of polysubstituted phenyl acetates via FeCl3-mediated domino reaction of 2-(aryl(piperidin-1-yl)methyl)phenols and 1,3-diketones

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Abstract A one-pot domino reaction involving Lewis acid-mediated nucleophilic-substitution/intramolecular-cyclization/reverse Claisen condensation of 2-(aryl(piperidin-1-yl)methyl)phenols and 1,3-diketones has been developed for the synthesis of 2-(3-oxo-1-phenylbutyl)phenyl acetates in good to excellent yields (77%–95%).… Click to show full abstract

Abstract A one-pot domino reaction involving Lewis acid-mediated nucleophilic-substitution/intramolecular-cyclization/reverse Claisen condensation of 2-(aryl(piperidin-1-yl)methyl)phenols and 1,3-diketones has been developed for the synthesis of 2-(3-oxo-1-phenylbutyl)phenyl acetates in good to excellent yields (77%–95%). The construction of the products has been accomplished via the domino generation of two new σ-bonds (C C and C O) with a wide functional group tolerance by using FeCl3 as mediation.

Keywords: methyl phenols; domino reaction; domino; aryl piperidin; piperidin methyl; phenols diketones

Journal Title: Tetrahedron
Year Published: 2017

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