Regioselective β-Csp3-Arylation of β-Alanine: An Approach for the Exclusive Synthesis of Diverse β-Aryl-β-amino Acids
- Resource Type
- Authors
- Namita Panwar; Wahajul Haq; Roopal Vaishnav; Sushobhan Chowdhury
- Source
- The Journal of Organic Chemistry. 84:2512-2522
- Subject
- Alanine
chemistry.chemical_classification
010405 organic chemistry
Chemistry
Aryl
Organic Chemistry
Regioselectivity
Peptide
010402 general chemistry
01 natural sciences
Combinatorial chemistry
0104 chemical sciences
Amino acid
chemistry.chemical_compound
Amide
- Language
- ISSN
- 1520-6904
0022-3263
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.