Visible-Light Photoredox Synthesis of Chiral α-Selenoamino Acids.
N-Acetoxyphthalimide derivatives of two genetically coded proteinogenic amino acids, l-aspartic acid and glutamic acid, were used as visible light photoredox chiral sources and radical precursors, diorganyl diselenides were used as the radical acceptors, and the diverse chiral α-selenoamino acid derivatives were prepared in good yields at room temperature. Furthermore, decarboxylative coupling of N-protected dipeptide active ester with diphenyl diselenide provided the corresponding selenodipeptide. The simple protocol, mild reaction conditions, high efficiency, and chiral keeping of this method make it an important strategy for the synthesis of chiral molecules.
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University , Beijing 100084, P. R. China.
Min
M
Jiang
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University , Beijing 100084, P. R. China.
Haijun
H
Yang
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University , Beijing 100084, P. R. China.
Hua
H
Fu
D000596:Amino Acids / Q000737:chemistry*; D008027:Light; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D055668:Photochemical Processes
D000596:Amino Acids; D016566:Organoselenium Compounds