Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry

被引:856
作者
Basavaiah, Deevi [1 ]
Reddy, Bhavanam Sekhara [1 ]
Badsara, Satpal Singh [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
ONE-POT SYNTHESIS; METHYL VINYL KETONE; N-SULFONATED IMINES; EFFICIENT STEREOSELECTIVE-SYNTHESIS; RING-CLOSING-METATHESIS; PHOSPHINE LEWIS-BASES; C BOND FORMATION; FRIEDEL-CRAFTS REACTION; BETA-HYDROXY ESTERS; JOHNSON-CLAISEN REARRANGEMENT;
D O I
10.1021/cr900291g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
There have been significant developments with respect to all the three essential components, namely activated alkenes or alkynes, electrophiles, and catalysts or catalytic systems. The acetates of the Baylis-Hillman alcohols derived from alkyl acrylate and aldehydes have been transformed into various poly-substituted phenol derivatives by Kim and coworkers via the alkylation using nitroalkanes, followed by Michael addition, cyclization, and aromatization strategies. Marko and co-workers have developed an interesting synthesis of bicyclic enedione, hydrindanones, and decalone derivatives from the Baylis-Hillman adducts obtained from cycloalkenones and terminal alkenals, following the reaction sequence shown in Schemes 291 and 292. Because of variations of parameters, flexibilities in using various combinations of activated alkenes, electrophiles, and catalysts, the understanding of the mechanism of this reaction has indeed become an intellectual puzzle.
引用
收藏
页码:5447 / 5674
页数:228
相关论文
共 1046 条
  • [1] Ozonolysis of Morita-Baylis-Hillman adducts originated from aromatic aldehydes:: an expeditious diastereoselective approach for the preparation of α,β-dihydroxy-esters
    Abella, Carlos A. M.
    Rezende, Patricia
    de Souza, Michele F. Lino
    Coelho, Fernando
    [J]. TETRAHEDRON LETTERS, 2008, 49 (01) : 145 - 148
  • [2] Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional β-isocupreidine derivatives
    Abermil, Nacim
    Masson, Geraldine
    Zhu, Jieping
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (38) : 12596 - +
  • [3] Study of the Baylis-Hillman reaction in a microreactor environment: First continuous production of Baylis-Hillman adducts
    Acke, Davy R. J.
    Stevens, Christian V.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (03) : 417 - 422
  • [4] STEREOSELECTIVE SYNTHESIS OF ALPHA,BETA-TRANS-SPIRO-BETA-LACTONES BY DIELS-ALDER CYCLOADDITION OF 1,3-DIENES TO ALPHA-METHYLENE-BETA-LACTONE AND THEIR DECARBOXYLATION BY PYROLYSIS TO (E)-ALKYLIDENECYCLOALKENES, A CONVENIENT OLEFINATION METHOD
    ADAM, W
    SALGADO, VON
    PETERS, EM
    PETERS, K
    VONSCHNERING, HG
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (06): : 1481 - 1486
  • [5] ADAM W, 1993, ANGEW CHEM INT EDIT, V32, P1737, DOI 10.1002/anie.199317371
  • [6] Efficient catalyst reuse by simple dissolution in non-conventional media
    Afonso, Carlos A. M.
    Branco, Luis C.
    Candeias, Nuno R.
    Gois, Pedro M. P.
    Lourenco, Nuno M. T.
    Mateus, Nuno M. M.
    Rosa, Joao N.
    [J]. CHEMICAL COMMUNICATIONS, 2007, (26) : 2669 - 2679
  • [7] Catalytic crossed Michael cycloisomerization of thioenoates:: Total synthesis of (±)-ricciocarpin A
    Agapiou, K
    Krische, MJ
    [J]. ORGANIC LETTERS, 2003, 5 (10) : 1737 - 1740
  • [8] Highly diastereoselective Diels-Alder reactions of Baylis-Hillman adducts
    Aggarwal, VK
    Patin, A
    Tisserand, S
    [J]. ORGANIC LETTERS, 2005, 7 (13) : 2555 - 2557
  • [9] Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis
    Aggarwal, VK
    Fulford, SY
    Lloyd-Jones, GC
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) : 1706 - 1708
  • [10] Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction:: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope
    Aggarwal, VK
    Emme, I
    Fulford, SY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) : 692 - 700