Regioselectivity Switch: Gold(I)-Catalyzed Oxidative Rearrangement of Propargyl Alcohols to 1,3-Diketones

被引：125
|
作者：
Hashmi, A. Stephen K. [1 ]
Wang, Tao [1 ]
Shi, Shuai [1 ]
Rudolph, Matthias [1 ]
机构：
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 17期
关键词：
CATALYZED RING EXPANSION; ONE-POT SYNTHESIS; GOLD CATALYSIS; BETA-DIKETONES; CYCLIZATION; KETONES; ROUTE;
D O I：
10.1021/jo301381z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The gold(I)-catalyzed oxidative rearrangement of propargyl alcohols provides an efficient and selective route to 1,3-diketones under mild conditions. Pyridine-N-oxides were used as external oxidants with, different from related substrates, no alkylidenecycloalkanones or oxetan-3-ones formed as side-products.
引用
收藏
页码：7761 / 7767
页数：7
相关论文
共 50 条
  • [41] Enantioselective Copper-Catalyzed Desymmetrization of 1,3-Diketones Involving Borylation of Styrenes
    Zheng, Purui
    Han, Xiaoyu
    Hu, Jiao
    Zhao, Xiaoming
    Xu, Tao
    ORGANIC LETTERS, 2019, 21 (15) : 6040 - 6044
  • [42] Catalytic Oxidative Cleavage of 1,3-Diketones to Carboxylic Acids by Aerobic Photooxidation with Iodine
    Tada, Norihiro
    Shomura, Motoki
    Cui, Lei
    Nobuta, Tomoya
    Miura, Tsuyoshi
    Itoh, Akichika
    SYNLETT, 2011, (19) : 2896 - 2900
  • [43] A novel synthesis of dihydrofuranyl alcohols through cascade reactions of 1,3-diketones with α,β-unsaturated epoxides
    Yu, Chengyu
    Yue, Guoren
    Yan, Penji
    Song, Hai
    Shi, Hucheng
    Wei, Yangfei
    Song, Zhengen
    Jia, Xin
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (23) : 5851 - 5855
  • [44] A route to hydroxylfluorenes: TsOH-mediated condensation reactions of 1,3-diketones with propargylic alcohols
    Yao, Liang-Feng
    Tan, Davin
    Miao, Xiaohe
    Huang, Kuo-Wei
    RSC ADVANCES, 2012, 2 (19) : 7594 - 7598
  • [45] Rhodium-Catalyzed Asymmetric Cycloisomerization of 1,3-Diketones with Keto-Vinylidenecyclopropanes: Synthesis of Enantiomerically Enriched Cyclic β-Amino Alcohols
    Xu, Chen
    Ning, Chao
    Yang, Song
    Wei, Yin
    Shi, Min
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (06) : 1727 - 1732
  • [46] Gold(I) catalyzed [1,3] O → C rearrangement of benzylvinyl ethers
    Kona, Chandrababu Naidu
    Patil, Mahesh N.
    Ramana, Chepuri V.
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (04): : 453 - 456
  • [47] Pd-catalyzed amidation of 1,3-diketones with CO and azides via a nitrene intermediate
    Gu, Zheng-Yang
    Chen, Jie
    Xia, Ji-Bao
    CHEMICAL COMMUNICATIONS, 2020, 56 (77) : 11437 - 11440
  • [48] Enantioselective Synthesis of Tricyclic β-Lactones by NHC-Catalyzed Desymmetrization of Cyclic 1,3-Diketones
    Shee, Sayan
    Mukherjee, Subrata
    Gonnade, Rajesh G.
    Biju, Akkattu T.
    ORGANIC LETTERS, 2020, 22 (14) : 5407 - 5411
  • [49] Cationic Iridium Complex-Catalyzed Intermolecular Hydroalkylation of Unactivated Alkenes with 1,3-Diketones
    Takeuchi, Ryo
    Sagawa, Jun
    Fujii, Masaki
    ORGANIC LETTERS, 2019, 21 (03) : 741 - 744
  • [50] Lanthanide-Catalyzed Oxyfunctionalization of 1,3-Diketones, Acetoacetic Esters, And Malonates by Oxidative C-O Coupling with Malonyl Peroxides
    Terent'ev, Alexander O.
    Vil', Vera A.
    Gorlov, Evgenii S.
    Nikishin, Gennady I.
    Pivnitsky, Kasimir K.
    Adam, Waldemar
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (03): : 810 - 823
12345