Pd-Catalyzed MIA-Directed Methoxylation of Phenylalanines: A Combined Experimental and Computational Study.

Keywords: methoxylation; palladium catalyst; MIA-directing group; DFT study; hydrogenation EN methoxylation palladium catalyst MIA-directing group DFT study hydrogenation 2547 2553 7 07/31/23 20230817 NES 230817 Graph The I o i -methoxy phenylalanine derivatives have been proven to be medicinal and synthetic valuable fragments, while, their preparation is relatively tricky. By using Raney Ni as a catalyst, a one-pot procedure incorporating the hydrogenation of MIA and protection of free amine proceeded smoothly at room temperature in an 88% yield, providing a short synthetic route for phenylalanine-containing dipeptides B 3 b . Methoxylation, palladium catalyst, MIA-directing group, hydrogenation, DFT study The reaction rate [K(CH SB 3 sb OH)/K(CH SB 3 sb OD)] was 3.07:1, which suggested that the oxhydryl cleavage from CH SB 3 sb OH was involved in the rate-limiting step. [Extracted from the article]