Electroreductive Ring-Opening Carboxylation of 1,3-Oxazolidin-2-ones with CO2 for Accessing β-Amino Acids

被引:3
|
作者
Tao, Li [1 ]
Liu, Xiao-Fei [1 ]
Ren, Bai-Hao [1 ]
Wang, He [1 ]
Sun, Hui-Qin [1 ]
Zhang, Ke [1 ]
Teng, Yong-Qiang [1 ]
Ren, Wei-Min [1 ]
Lu, Xiao-Bing [1 ]
Zhang, Wen-Zhen [1 ]
机构
[1] Dalian Univ Technol, Frontiers Sci Ctr Smart Mat, State Key Lab Fine Chem, Dalian 116024, Liaoning, Peoples R China
基金
中国国家自然科学基金;
关键词
ELECTROCARBOXYLATION;
D O I
10.1021/acs.orglett.3c04007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Electrocarboxylation of the C(sp(3))-O bond in 1,3-oxazolidin-2-ones with CO2 to achieve beta-amino acids is developed. The C-O bond in substrates can be selectively cleaved via the single electron transfer on the surface of a cathode or through a CO2 center dot (-) intermediate under additive-free conditions. A great diversity of beta-amino acids can be obtained in a moderate to excellent yield and readily converted to various biologically active compounds.
引用
收藏
页码:542 / 546
页数:5
相关论文
共 50 条
  • [41] Electroreductive Carboxylation of Propargylic Acetates with CO2: Access to Tetrasubstituted 2,3-Allenoates
    Qin, Jing-Hao
    Xiong, Zhi-Qiang
    Cheng, Chaozhihui
    Hu, Ming
    Li, Jin-Heng
    ORGANIC LETTERS, 2023, 25 (51) : 9176 - 9180
  • [42] An Exploration of the Metal Oxide-assisted Decomposition and Rearrangement of N-Acyl-1,3-oxazolidin-2-ones Leading to 2-Aryl-2-oxazolines [1]
    Deshpande, Ankur A.
    Gossage, Robert A.
    Jackson, Sarah M.
    Quail, J. Wilson
    Sadowy, Amber L.
    Yadav, Paras N.
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2009, 64 (09): : 1046 - 1052
  • [43] The reaction of acetylenic amines with tetraethylammonium carbonate and hydrogen carbonate; Synthesis of 5-methylene-1,3-oxazolidin-2-ones
    Arcadi, A
    Inesi, A
    Marinelli, F
    Rossi, L
    Verdecchia, M
    SYNLETT, 2005, (01) : 67 - 70
  • [44] Electrochemically promoted C-N bond formation from acetylenic amines and CO2.: Synthesis of 5-methylene-1,3-oxazolidin-2-ones
    Feroci, M
    Orsini, M
    Sotgiu, G
    Rossi, L
    Inesi, A
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (19): : 7795 - 7798
  • [45] Two-in-One: Photothermal Ring-Opening Copolymerization of CO2 and Epoxides
    Zhuo, Chunwei
    Cao, Han
    You, Huai
    Liu, Shunjie
    Wang, Xianhong
    Wang, Fosong
    ACS MACRO LETTERS, 2022, 11 (07) : 941 - 947
  • [46] Formate and CO2 Enable Reductive Carboxylation of Imines: Synthesis of Unnatural α-Amino Acids
    Xu, Pei
    Liu, Wen-Wen
    Hao, Tian-Zi
    Liu, Yi-Qin
    Jiang, Hui-Xian
    Xu, Jing
    Li, Jin-You
    Yin, Long
    Zhu, Song-Lei
    Zhu, Xu
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (14): : 9750 - 9754
  • [47] SELECTIVITY OF ANIONIC ACTIVATION BY FLUORIDE-ION IN SOLID LIQUID-SYSTEMS - SYNTHESIS OF TETRAMIC ACIDS AND 4-METHYLENE-1,3-OXAZOLIDIN-2-ONES
    SEBTI, S
    FOUCAUD, A
    JOURNAL OF CHEMICAL RESEARCH-S, 1987, (03): : 72 - 73
  • [48] RING-OPENING OF 2,3-DIPHENYLCYCLOPROPYLLITHIUM TO 1,3-DIPHENYLALLYLLITHIUM COMPOUNDS
    BOCHE, G
    BUCKL, K
    MARTENS, D
    SCHNEIDER, DR
    WAGNER, HU
    CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (08): : 2961 - 2996
  • [49] 3-Benzyl-1,3-oxazolidin-2-ones as mGluR2 positive allosteric modulators: Hit-to lead and lead optimization
    Duplantier, Allen J.
    Efremov, Ivan
    Candler, John
    Doran, Angela C.
    Ganong, Alan H.
    Haas, Jessica A.
    Hanks, Ashley N.
    Kraus, Kenneth G.
    Lazzaro, John T., Jr.
    Lu, Jiemin
    Maklad, Noha
    McCarthy, Sheryl A.
    O'Sullivan, Theresa J.
    Rogers, Bruce N.
    Siuciak, Judith A.
    Spracklin, Douglas K.
    Zhang, Lei
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (09) : 2524 - 2529
  • [50] Concise One-step Synthesis of 4-Arylidene-1,3-oxazolidin-2-ones with Internal Propargylic Alcohols and Isocyanates
    Kim, Won Sun
    Yoon, Eunyoung
    Jo, Kyoung A.
    Kang, Eun Joo
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (08): : 3158 - 3160