Bronsted base-catalyzed annulation of allyl ketones and alkynyl 1,2-diketones

被引：16
作者：
Kong, Xiangwen [1 ]
Song, Jinshuai [1 ]
Liu, Jian [1 ]
Meng, Miao [2 ]
Yang, Shuang [1 ]
Zeng, Min [3 ]
Zhan, Xinyue [3 ]
Li, Chunsen [1 ]
Fang, Xinqiang [1 ]
机构：
[1] Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, State Key Lab Struct Chem, Fuzhou 350100, Fujian, Peoples R China
[2] Jinan Univ, Dept Chem, Guangzhou 510632, Guangdong, Peoples R China
[3] Fuzhou Univ, Coll Chem, Fuzhou 350116, Fujian, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 34期
基金：
中国国家自然科学基金;
关键词：
VINYLOGOUS ALDOL REACTION; PHASE-TRANSFER CATALYSIS; MICHAEL REACTIONS; MANNICH REACTION; TRANSFORMATIONS; CONSTRUCTION; DERIVATIVES; ALKYLATION; ACTIVATION; YNEDIONES;
D O I：
10.1039/c8cc01020j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The discovery of new reaction modes mediated by easily available substrates is an important research topic in organic synthesis. Allyl ketones and related compounds have been demonstrated to undergo gamma- or alpha-selective additions to different electrophiles. We disclose here the Bronsted base-catalyzed reaction of allyl ketones and alkynyl 1,2-diketones, which undergo a unique alpha-selective addition/intramolecular aldol-type annulation/C-C bond cleavage process, and a series of 2-acyloxycyclopent-3-enones can be obtained under very mild conditions.
引用
收藏
页码：4266 / 4269
页数：4
相关论文
共 38 条
  • [1] [Anonymous], 2012, SYNTHESIS
  • [2] Catalytic Enantioselective γ-Selective Additions of 2-Allylazaarenes to Activated Ketones
    Bai, Xiangbin
    Zeng, Guangkuo
    Shao, Tianju
    Jiang, Zhiyong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (13) : 3684 - 3688
  • [3] An unusual erythrolide containing a bicycle [9.2.1.] tetradecane skeleton
    Banjoo, D
    Maxwell, AR
    Mootoo, BS
    Lough, AJ
    McLean, S
    Reynolds, WF
    [J]. TETRAHEDRON LETTERS, 1998, 39 (12) : 1469 - 1472
  • [4] Development of Enantioselective Synthetic Routes to the Hasubanan and Acutumine Alkaloids
    Calandra, Nicholas A.
    King, Sandra M.
    Herzon, Seth B.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) : 10031 - 10057
  • [5] The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress
    Casiraghi, Giovanni
    Battistini, Lucia
    Curti, Claudio
    Rassu, Gloria
    Zanardi, Franca
    [J]. CHEMICAL REVIEWS, 2011, 111 (05) : 3076 - 3154
  • [6] "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation
    Chen, Peng-hao
    Billett, Brent A.
    Tsukamoto, Tatsuhiro
    Dong, Guangbin
    [J]. ACS CATALYSIS, 2017, 7 (02): : 1340 - 1360
  • [7] Psilostachyin, acetylated pseudoguaianolides and their analogues: Preparation and evaluation of their anti-inflammatory potential
    Chib, Renu
    Shah, Bhahwal Ali
    Anand, Naveen
    Pandey, Anjali
    Kapoor, Kamini
    Bani, Sarang
    Gupta, Vivek K.
    Rajnikant
    Sethi, Vijay K.
    Taneja, Subhash Chandra
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (16) : 4847 - 4851
  • [8] Acylvinyl and vinylogous synthons
    Chinchilla, R
    Nájera, C
    [J]. CHEMICAL REVIEWS, 2000, 100 (06) : 1891 - 1928
  • [9] Denmark SE, 2005, ANGEW CHEM INT EDIT, V44, P4682, DOI 10.1002/anie.200462338
  • [10] Rationally Designed Multifunctional Supramolecular Iminium Catalysis: Direct Vinylogous Michael Addition of Unmodified Linear Dienol Substrates
    Gu, Yun
    Wang, Yao
    Yu, Tian-Yang
    Liang, Yong-Min
    Xu, Peng-Fei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (51) : 14128 - 14131
1234