We report the construction of racemic and enantiopure biaryl unnatural amino acid derivatives via the palladium-catalyzed stereoselective sp 3 CÀ H activation and arylation of amino acid derivatives with iodobiaryls. The synthesis of biaryl motif installed (DL-), L-and D-amino acid derivatives including norvaline, phenylalanine, leucine, norleucine and 2-aminooctanoic acid with anti stereochemistry is reported. The synthesis of alanine derivatives with two biaryl motifs and aminoalkanoic acids with biaryl motifs is also shown. The CÀ H arylation of enantiopure carboxamides gave biaryl amino acid derivatives with good enantiopurity. Removal of the directing group 8aminoquinoline, deprotection of the phthalimide moiety, and the preparation of biaryl amino acid derivatives containing free amino-and carboxylate groups are also reported. The stereochemistry (anti) of representative major diastereomers was unequivocally ascertained from X-ray structure analysis. Biaryl amino acids/peptides are important motifs in medicinal chemistry, and this work therefore represents a contribution towards enriching the library of biaryl amino acids.
We report the synthesis of carbazole-based unnatural α-amino acid and non-α-amino acid derivatives via the Pd(II)-catalyzed bidentate directing group 8-aminoquinoline-aided β-C(sp3)-H activation/functionalization tactic. Various N-phthaloyl, DL-, L- and D-carboxamides derived...
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