Synergistic Pd/Cu catalysis for stereoselective allylation of vinylethylene carbonates with glycine iminoesters: Enantioselective access to diverse trisubstituted allylic amino acid derivatives

Miaolin Ke; Zhigang Liu; Ke Zhang; Sheng Zuo; Fener Chen

Green Synthesis and Catalysis (May 2021)

Synergistic Pd/Cu catalysis for stereoselective allylation of vinylethylene carbonates with glycine iminoesters: Enantioselective access to diverse trisubstituted allylic amino acid derivatives

Miaolin Ke,
Zhigang Liu,
Ke Zhang,
Sheng Zuo,
Fener Chen

Affiliations

Miaolin Ke: Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China; Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China; Institute of Pharmaceutical Science and Technology, Zhejiang University of Technology, Hangzhou 310014, China
Zhigang Liu: Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China; Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China
Ke Zhang: Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China; Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China
Sheng Zuo: Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China; Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China
Fener Chen: Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China; Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China; Institute of Pharmaceutical Science and Technology, Zhejiang University of Technology, Hangzhou 310014, China; Corresponding author. Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China.

Journal volume & issue: Vol. 2, no. 2
pp. 228 – 232

Abstract

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We reported a synergistic Pd/Cu catalyzed enantioselective decarboxylative allylation of vinylethylene carbonates with glycine iminoesters, which provides facile access to non-proteinogenic diverse trisubstituted allylic amino acid derivatives in high yields, exclusive regioselectivities and excellent stereoselectivities. This reaction tolerates a wide range of γ and β-aryl substituted vinylethylene carbonates with either electron-donating or electron-withdrawing groups. Significantly, this method was proven to be sufficient in the gram scale synthesis of chiral trisubstituted allylic amino acid while retaining the enantioselectivity and geometric control.

Published in Green Synthesis and Catalysis

ISSN: 2666-5549 (Online)
Publisher: KeAi Communications Co. Ltd.
Country of publisher: China
LCC subjects: Technology: Chemical technology; Science: Chemistry: Organic chemistry: Biochemistry
Website: https://www.keaipublishing.com/en/journals/green-synthesis-and-catalysis/

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