Synthesis of β-hydroxy-α-amino acid derivatives by the cross-dehydrogenative coupling of N-arylglycine esters with α-hydroxy ketones

A formal cross-dehydrogenative coupling reaction between α-hydroxy ketones and N-arylglycine derivatives for the synthesis of various β-hydroxy-α-amino acid derivatives is disclosed. The compatibility of substrate and oxidant in this reaction is achieved by controlling the dosing sequence, and the p...

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Bibliographic Details
Published in:Tetrahedron 2021-11, Vol.100, p.132491, Article 132491
Main Authors: Wang, Junjiao, Lv, Yuyu, Shang, Yongwei, Deng, Zhoubin, Zhang, Jianzhong, Ma, Xue-E, Wang, Ke-Hu, Huang, Danfeng, Su, Yingpeng, Hu, Yulai
Format: Article
Language:English
Subjects:
Cross dehydrogenative coupling reaction
In situ oxidation
Nucleophilic addition
β- hydroxy-α-amino acid
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Summary:A formal cross-dehydrogenative coupling reaction between α-hydroxy ketones and N-arylglycine derivatives for the synthesis of various β-hydroxy-α-amino acid derivatives is disclosed. The compatibility of substrate and oxidant in this reaction is achieved by controlling the dosing sequence, and the products are successfully obtained in 29–93% yields. This work provides a new method for the synthesis of β-hydroxy-α-amino acid derivatives which possesses high efficiency, convenience, and atom economy. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2021.132491