Photoinduced Electron Transfer Promoted Radical Ring Expansion and Cyclization Reactions of α-(ω-Carboxyalkyl) β-Keto Esters

被引:34
|
作者
Nishikawa, Keisuke [1 ]
Ando, Tomoki [1 ]
Maeda, Kousuke [1 ]
Morita, Toshio [1 ]
Yoshimi, Yasuharu [1 ]
机构
[1] Univ Fukui, Grad Sch Engn, Dept Appl Chem & Biotechnol, Fukui 9108507, Japan
关键词
CARBOXYLIC-ACIDS; PHOTOCHEMICAL DECARBOXYLATION; ROUTE; ALKYL;
D O I
10.1021/ol303460u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photoinduced electron transfer (PET) promoted decarboxylation of alpha-(omega-carboxyalkyl) beta-keto esters undergoes radical ring expansion and cyclization reactions. This mild and environmentally friendly method can provide one-carbon expanded gamma-keto esters and bicyclic alcohols, and the product distribution is strongly dependent on the length of the alkyl chain containing the terminal carboxylate group.
引用
收藏
页码:636 / 638
页数:3
相关论文
共 50 条
  • [31] Cyclization reactions of diazoketo esters promoted by fluorous catalysts.
    Russak, JA
    Schoffstall, AM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U338 - U338
  • [32] RING EXPANSION REACTIONS OF CYCLIC BETA - KETO PHOSPHONATES
    KULKARNI, VR
    RUDER, SM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 403 - ORGN
  • [33] Synthesis and Cyclization Reactions with Pyrazolopyrimidinyl Keto-esters and their Enzymaic Activity
    Awas, Mohamed Abdel Hamid Abd el Gawaad
    ACTA CHIMICA SLOVENICA, 2008, 55 (03) : 492 - 501
  • [34] Metallic salt promoted radical cyclization of β-keto carboxamides and their corresponding β-enamino carboxamides
    Cossy, J
    Bouzide, A
    Leblanc, C
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22): : 7257 - 7265
  • [35] RING EXPANSIONS VIA PHOTOINDUCED SINGLE ELECTRON-TRANSFER PROMOTED OPENING OF CYCLOPROPYL ETHERS
    GASSMAN, PG
    BURNS, SJ
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23): : 5576 - 5578
  • [36] PHOTOINDUCED ELECTRON-TRANSFER REACTIONS
    SUTIN, N
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1977, 174 (SEP): : 103 - 103
  • [37] Photoinduced electron transfer reactions of phthalimides
    Bartoschek, A
    Griesbeck, AG
    Oelgemöller, M
    JOURNAL OF INFORMATION RECORDING, 2000, 25 (1-2): : 119 - 126
  • [38] Stereocontrol strategy in photoinduced electron transfer cyclization reaction
    Zhang, Rong-Hua
    Zeng, Yuan
    Jiang, Zhi-Qin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (03) : 407 - 415
  • [39] PHOTOINDUCED ELECTRON-TRANSFER-INITIATED AROMATIC CYCLIZATION
    MARUYAMA, K
    OTSUKI, T
    TAI, S
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (01): : 52 - 60
  • [40] Photoinduced radical cascade cyclization of acetylenic acid esters with oxime esters to access cyanalkylated coumarins
    Yang, Xiao
    Xia, Yanping
    Tong, Jinghui
    Ouyang, Lu
    Lai, Yinlong
    Luo, Renshi
    Liao, Jianhua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (26) : 5239 - 5244