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Pd-catalyzed directed ortho-C-H alkenylation of phenylalanine derivatives

AutorGarcía-Rubia, Alfonso; Laga, Eduardo ; Cativiela, Carlos ; Urriolabeitia, Esteban P. ; Gómez-Arrayás, Ramón; Carretero, Juan Carlos
Fecha de publicación2015
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 80(6): 3321-3331 (2015)
ResumenA practical Pd-catalyzed ortho-olefination of enantioenriched N-(SO2Py)-protected aryl-alanine and norephedrine derivatives with electron-deficient alkenes has been developed using N-fluoro-2,4,6-trimethylpyridinium triflate as the terminal oxidant. The reaction occurs efficiently with excellent monosubstitution selectivity and without loss of enantiopurity. This cross-coupling proved to be broad in scope, tolerating a variety of steric and electronic changes to both coupling partners. Removal of the directing group under mild conditions provides access to optically active tetrahydroisoquinoline-3-carboxylic acid derivatives (Tics) with good diastereocontrol and with very small erosion of enantiomeric purity.
Versión del editorhttps://doi.org/10.1021/jo502912m
URIhttp://hdl.handle.net/10261/154769
Identificadoresdoi: 10.1021/jo502912m
e-issn: 1520-6904
issn: 0022-3263
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