Synthesis of Diverse Oxetane Amino Acids via Visible-Light-Induced Photocatalytic Decarboxylative Giese-Type Reaction  

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作  者:Haoliang Shi Yi Wan Yongqiang Zhang 

机构地区:[1]Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism,Shanghai Key Laboratory of New Drug Design,and School of Pharmacy,East China University of Science and Technology,Shanghai,200237 China

出  处:《Chinese Journal of Chemistry》2024年第12期1341-1346,共6页中国化学(英文版)

基  金:Financial support from the program of the National Natural Science Foundation of China(21871086 and 22171080,Y-Q.Z.);Natural Science Foundation of Shanghai(23ZR1417200,Y.-Q.Z.)isgratefullyacknowledged.

摘  要:The divergent synthesis of versatile 3,3′-disubstituted oxetane amino acids by utilizing visible-light-induced photocatalytic decarboxylative Giese-type reaction has been demonstrated.3-Methyleneoxetane-derived substrates are readily available in a single-step and highly reactive as radical acceptors,allowing the production of versatile oxetaneγ-andα-amino acids in high yields.A distinct ring strain release-driven radical addition mechanism was preliminarily revealed.The preparative power was further highlighted by the application in the synthesis of oxetane-containing dipeptides and azetidine amino acids,as well as the transformation of the product into novel oxetane-containing spiro-heterocycle pharmacophore.

关 键 词:Photoredox catalysis Decarboxylative Giese-type reaction Oxetane amino acids Amino acids Synthesis Radical reactions 

分 类 号:O62[理学—有机化学]

 

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