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Selective Functionalization of Achmatowicz Rearrangement Products by Reactions with Potassium Organotrifluoroborates under Transition-Metal-Free Conditions

Silvia Roscales, Víctor Ortega, Aurelio G. Csák˙*

*Instituto Pluridisciplinar, Universidad Complutense, Campus de Excelencia Internacional Moncloa, Paseo de Juan XXIII, 1, 28040 Madrid, Spain, Email:

S. Roscales, V. Ortega, A. G. Csák˙, J. Org. Chem., 2018, 83, 11425-11436.

DOI: 10.1021/acs.joc.8b01643

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Synthetic transformations of the products of the Achmatowicz rearrangement with potassium organotrifluoroborates in the absence of transition metals provide dihydropyranones (2,6-trans), tetrahydropyranones (2,3-cis-2,6-cis) or functionalized 1,4-dicarbonyl compounds depending on the reaction conditions and the substitution pattern. The method has also been adapted for the one-pot synthesis of functionalized pyrroles.

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Key Words


ID: J42-Y2018