Citation: Xi Lu, Bin Xiao, Rui Shang, Lei Liu. Synthesis of unnatural amino acids through palladium-catalyzed C(sp³)-H functionalization[J]. Chinese Chemical Letters, ;2016, 27(03): 305-311. doi: 10.1016/j.cclet.2015.12.021 shu

Synthesis of unnatural amino acids through palladium-catalyzed C(sp³)-H functionalization

Xi Lu ^a ,
Bin Xiao ^b ,
Rui Shang ^b ,
Lei Liu ^a,,

a.
a. Tsinghua-Peking Center for Life Sciences, Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China;
b.
b. Department of Chemistry, University of Science and Technology of China, Hefei 230026, China

Corresponding author: Lei Liu,
Received Date: 16 October 2015
Available Online: 29 November 2015

Unnatural α-amino acids have been extensively used in the modern drug discovery and protein engineering studies. They have also found applications in the development of chiral molecular catalysts and the total synthesis of diverse natural products. Accordingly the development of cost-effective approaches for the preparation of unnatural α-amino acids has received increasing attentions. Among all the available methods for this purpose, direct C-H functionalization of simple amino acids represents one of the most attractive approaches because it exhibits good atom-economy and step-efficiency. In particular, selective functionalization of either the primary or secondary C(sp³)-H bonds in the amino acids has been explored to make versatile C-C, C-N, C-O, C-B and C-F bonds to modify the side chain of amino acids and even peptides. The present review surveys the recent advances of synthesis of chiral unnatural α-amino acids and peptides through palladium-catalyzed functionalization of un-activated C(sp³)-H bonds.
- Palladium,
- C-H functionalization,
- Unnatural amino acids,
- Carbon-carbon coupling,
- Carbon-heteroatom coupling
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Synthesis of unnatural amino acids through palladium-catalyzed C(sp3)-H functionalization

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Synthesis of unnatural amino acids through palladium-catalyzed C(sp³)-H functionalization