A Unique Cascade Reaction between 3-Arylprop-2-inylcarboxylates and Benzaldehydes Leading to the Formation of Morita-Baylis-Hillman Adducts

被引:15
|
作者
Karpaviciene, Ieva [1 ]
Cikotiene, Inga [1 ]
机构
[1] Vilnius State Univ, Fac Chem, Dept Organ Chem, LT-03225 Vilnius, Lithuania
关键词
PHENYL VINYL KETONE; ALDEHYDES; ACRYLATE; THIOACRYLATE; DIMERIZATION; CATALYSIS; ALKYNES; BF3;
D O I
10.1021/ol303319a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
During an alkyne-carbonyl metathesis reaction between electron-rich 3-arylprop-2-inylcarboxylates and electron-poor benzaldehydes, a smooth migration of carboxylate groups takes place. This unique cascade reaction allows the formation of Morita-Baylis-Hillman (MBH) adducts unavailable via a traditional MBH reaction.
引用
收藏
页码:224 / 227
页数:4
相关论文
共 50 条
  • [41] Synthesis of 3-(γ, δ-Disubstituted)allylidene-2-Oxindoles from Isatins by Wittig Reaction with Morita-Baylis-Hillman Bromides
    Moon, Hye Ran
    Kim, Ko Hoon
    Lee, Junseong
    Kim, Jae Nyoung
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (01): : 219 - 225
  • [42] Chiral phosphine-squaramide-catalyzed Morita-Baylis-Hillman reaction: enantioselective synthesis of 3-hydroxy-2-oxindoles
    Qian, Jing-Ying
    Wang, Ci-Ci
    Sha, Feng
    Wu, Xin-Yan
    RSC ADVANCES, 2012, 2 (14) : 6042 - 6048
  • [43] C-C BOND FORMATION ON 5-POSITION OF URIDINE RING BY MORITA-BAYLIS-HILLMAN TYPE REACTION
    Monguchi, Yasunari
    Yasunaga, Kanoko
    Tsunoda, Takashi
    Ando, Takayuki
    Maegawa, Tomohiro
    Hirota, Kosaku
    Sajiki, Hironao
    HETEROCYCLES, 2010, 80 (01) : 537 - 555
  • [44] Selection of 2D/3D molecular descriptors and QSAR modeling of aromatic Morita-Baylis-Hillman adducts with leishmanicidal activities
    Alencar Filho, Edilson B.
    Weber, Karen C.
    Vasconcellos, Mario L. A. A.
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (12) : 5328 - 5335
  • [45] Dual Iminium- and Lewis Base Catalyzed Morita-Baylis-Hillman Reaction on Cyclopent-2-enone
    Innocenti, Riccardo
    Menchi, Gloria
    Trabocchi, Andrea
    SYNLETT, 2018, 29 (06) : 820 - 824
  • [46] Morita-Baylis-Hillman reaction of indole-2-carboxaldehyde: new vistas for indole-annulated systems
    Biswas, Subhasish
    Singh, Virender
    Batra, Sanjay
    TETRAHEDRON, 2010, 66 (39) : 7781 - 7786
  • [47] Asymmetric [3+2]-Cycloaddition of Morita-Baylis-Hillman Carbonates with Maleimides Catalyzed by Chiral Ferrocenylphosphines
    Tu, Aiping
    Hu, Haiwen
    Du, Tieqi
    Zhong, Weihui
    SYNTHETIC COMMUNICATIONS, 2014, 44 (23) : 3392 - 3399
  • [48] Enantioselective Radical SN2-Type Alkylation of Morita-Baylis-Hillman Adducts Using Dual Photoredox/Palladium Catalysis
    Bai, Xiangbin
    Qian, Linlin
    Zhang, Hong-Hao
    Yu, Shouyun
    ORGANIC LETTERS, 2021, 23 (21) : 8322 - 8326
  • [49] Diastereoselective allylic rearrangement of Morita-Baylis-Hillman C-adducts: a facile access to functionalized 1, 2-dihydroisoquinolines
    Xu, Qiu-Qin
    Qin, Tian-You
    Wang, Ting-Ting
    Wang, Tai-Jing
    Liao, Wei-Wei
    TETRAHEDRON, 2015, 71 (06) : 941 - 948
  • [50] Exploratory applications of 2-nitrobenzaldehyde-derived Morita-Baylis-Hillman adducts as synthons in the construction of drug-like scaffolds
    Idahosa, Kenudi C.
    Davies-Coleman, Michael T.
    Kaye, Perry T.
    SYNTHETIC COMMUNICATIONS, 2019, 49 (03) : 417 - 430