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Nickel Photocatalytic Access to β-Arylated β-Amino Acids
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DOI：10.1002/adsc.70586.png)
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Abstract
En 中文
Noncanonical amino acids are prevalent handles in drug discovery to improve pharmacological properties. Here, we present a nickel-photocatalytic method that yields β-arylated β-amino acids from abundant aspartic acid as natural amino acid and widely available (hetero)aryl bromides as cross-coupling electrophiles. Utilizing dimethoxyethane as solvent and tert-butyl tetramethylguanidine (BTMG) as base gives highest yields, and various functional groups were tolerated in the final amino acid products. More than 21 non-canonical amino acids were obtained in up to good yields, and diversification enabled the synthesis of bioactive derivatives, ready for follow-up application. This concept of using naturally occurring amino acids as starting materials allows for access to non-canonical counterparts under mild and photocatalytic control.
Keywords:
arylation
cross-coupling
dimethoxyethane
nickel catalysis
noncanonical amino acids
Journal
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4
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424
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