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Regioselective β-Csp³-Arylation of β-Alanine: An Approach for the Exclusive Synthesis of Diverse β-Aryl-β-amino Acids
- Chowdhury, Sushobhan, Vaishnav, Roopal, Panwar, Namita, Haq, Wahajul
- Journal of organic chemistry 2019 v.84 no.5 pp. 2512-2522
- acids, aminoquinolines, arylation, catalytic activity, chemical structure, engineering, organic chemistry, palladium, peptides, regioselectivity
- An approach for the synthesis of a variety of new β-aryl-β-amino acids has been developed via a palladium-catalyzed auxiliary-directed regioselective Csp³-H arylation of the unactivated β-methylene bond of β-alanine. The use of 8-aminoquinoline amide as an auxiliary efficiently directs the desired regioselective β-Csp³-H functionalization. The developed protocol enables the easy and straightforward access to several high-value β-aryl-β-amino acids useful for peptide engineering, starting from inexpensive and readily available β-alanine precursors in moderate to excellent yields.