Citation: Yang Zhou, Hang Chen, Panpan Lei, Chunming Gui, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fener Chen. Palladium-catalyzed base- and solvent-controlled chemoselective allylation of amino acids with allylic carbonates[J]. Chinese Chemical Letters, ;2022, 33(11): 4850-4855. doi: 10.1016/j.cclet.2022.02.029 shu

Palladium-catalyzed base- and solvent-controlled chemoselective allylation of amino acids with allylic carbonates

Yang Zhou ^{b, 1} ,
Hang Chen ^{b, 1} ,
Panpan Lei ^b ,
Chunming Gui ^a ,
Haifeng Wang ^a ,
Qiongjiao Yan ^a ,
Wei Wang ^{a, *,} ,
Fener Chen ^{a, c, d, *,}

a.
Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, China
b.
Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637009, China
c.
Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China
d.
Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai 200433, China

wang520520wei@163.com

rfchen@fudan.edu.cn

Received Date: 22 December 2021
Revised Date: 11 February 2022
Accepted Date: 14 February 2022
Available Online: 18 February 2022

Figures(6)

The utilization of readily available amino acids, which is not only an oxygen nucleophile but also a nitrogen nucleophile, in palladium-catalyzed allylic substitution is realized under mild conditions. The chemoselectivity and multiple allylation are controlled by adjusting the reaction conditions. This represents the first example of this convenient access to valuable N,O-diallylated amino acids. Under the title conditions, a range of amino acids (α-, β-, γ-) and dipeptides can be readily converted in to the corresponding allylic products with excellent yields (67 examples, up to 99% yield) as well as good functional group tolerance.
- Allylation,
- Amino acid,
- Carbonates,
- Chemoselectivity,
- Palladium
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