化学
光催化
烷基化
催化作用
氨基酸
光催化
小学(天文学)
组合化学
氢键
有机化学
立体化学
药物化学
分子
生物化学
天文
物理
作者
James D. Grayson,Alexander J. Cresswell
出处
期刊:Tetrahedron
[Elsevier]
日期:2021-02-01
卷期号:81: 131896-131896
被引量:12
标识
DOI:10.1016/j.tet.2020.131896
摘要
We report a simple photocatalytic protocol for the direct synthesis of γ-amino phosphonates via the α-C–H alkylation of unprotected, aliphatic primary amines with diethyl vinylphosphonate. These motifs are valuable bioisosteres of γ-amino acids and O-phosphorylated amino alcohols. Visible-light photoredox catalysis in combination with hydrogen atom transfer (HAT) catalysis is used to access the necessary α-amino radical intermediates for C–C bond formation. The procedure is also demonstrated on gram-scale in continuous flow for the synthesis of a racemic, protected derivative of the mGlu agonist 2-amino-4-phosphonobutyric acid (AP4).
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