An efficient Darzens reaction promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)

被引：3
|
作者：
Luo, Juan [1 ]
Hu, Lanfang [1 ]
Zhang, Minghao [1 ]
Tang, Qiang [1 ]
机构：
[1] Chongqing Med Univ, Coll Pharm, Chongqing Res Ctr Pharmaceut Engn, Ctr Lab Teaching & Management, 1 Yixueyuan Rd, Chongqing 400016, Peoples R China
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 30期
关键词：
DBU; Darzens reaction; alpha; beta-Epoxy ketone; alpha-Haloketone; ASYMMETRIC DARZENS; EPOXIDE; CONDENSATION; ALDEHYDES; CATALYSTS; AGENT;
D O I：
10.1016/j.tetlet.2019.06.034
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient DBU promoted Darzens reaction utilising alpha-haloketones containing an enolizable alpha'-hydrogen is reported. This method diastereoselectively afforded the corresponding alpha,beta-epoxy ketones good to excellent yields in an one-pot reaction without using any transition metals or additives. Furthermore, haloketones without an alpha'-hydrogen are also applicable in this reaction. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1949 / 1951
页数：3
相关论文
共 50 条
  • [1] The reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with carbon dioxide
    Heldebrant, DJ
    Jessop, PG
    Thomas, CA
    Eckert, CA
    Liotta, CL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13): : 5335 - 5338
  • [2] DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) - A nucleophillic base
    Ghosh, N
    [J]. SYNLETT, 2004, (03) : 574 - 575
  • [3] 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Decomposition of Difluorocarbene and the Subsequent Trifluoromethylation
    Zheng, Jian
    Lin, Jin-Hong
    Deng, Xiao-Yun
    Xiao, Ji-Chang
    [J]. ORGANIC LETTERS, 2015, 17 (03) : 532 - 535
  • [4] 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted efficient and versatile aza-Michael addition
    Yeom, Chang-Eun
    Kim, Mi Jeong
    Kim, B. Moon
    [J]. TETRAHEDRON, 2007, 63 (04) : 904 - 909
  • [5] 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU): A Versatile Reagent in Organic Synthesis
    Nand, Bhaskara
    Khanna, Garima
    Chaudhary, Ankita
    Lumb, Anshika
    Khurana, Jitender M.
    [J]. CURRENT ORGANIC CHEMISTRY, 2015, 19 (09) : 790 - 812
  • [6] DIALKYLATION IN PRESENCE OF 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE
    OEDIGER, H
    MOLLER, F
    [J]. ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1976, (02): : 348 - 351
  • [7] 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU): A highly efficient catalyst in glycerol carbonate synthesis
    Munshi, Mudassir K.
    Gade, Swapna M.
    Mane, Manoj V.
    Mishra, Deepti
    Pal, Sourav
    Vanka, Kumar
    Rane, Vilas H.
    Kelkar, Ashutosh A.
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 391 : 144 - 149
  • [8] 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE AS A DIFUNCTIONAL NUCLEOPHILE
    CHAMBERS, RD
    ROCHE, AJ
    BATSANOV, AS
    HOWARD, JAK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) : 2055 - 2056
  • [9] A cautionary note on the use of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in conjunction with chlorophosphates
    Kers, A
    Kers, I
    Bollmark, M
    Stawinski, J
    [J]. ACTA CHEMICA SCANDINAVICA, 1998, 52 (12): : 1405 - 1406
  • [10] 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as ligand for atom transfer radical polymerization (ATRP)
    Fournier, D
    Romagné, ML
    Pascual, S
    Montembault, W
    Fontaine, L
    [J]. EUROPEAN POLYMER JOURNAL, 2005, 41 (07) : 1576 - 1581
12345