Cascade Halo-Michael/Aldol Reaction and Its Application in Synthesis

被引:1
|
作者
Dai, Yihua [1 ]
Shen, Yanfeng [1 ]
Gao, Shuanhu [1 ,2 ]
机构
[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
[2] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
halo-michael/aldol reaction; cascade reaction; Lewis acid; application; synthesis; BAYLIS-HILLMAN REACTION; ENANTIOSELECTIVE TOTAL-SYNTHESIS; Z/E STEREOSELECTIVE-SYNTHESIS; ALDOL REACTION; ALPHA; BETA-ACETYLENIC KETONES; TITANIUM(IV) CHLORIDE; ASYMMETRIC-SYNTHESIS; BIOLOGICAL EVALUATION; STRUCTURAL REVISION; PAF ANTAGONISTS;
D O I
10.6023/cjoc201803005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Michael addition and aldol reaction are among the most basic and commoly used reactions. Cascade halo-Michael/Aldol reaction can effectively improve the atomic economy and step economy of organic synthesis. After the Michael addition of alpha,beta-unsaturated compound with halide ion (Cl-, Br-, I-), the reactive intermediate reacts with aldehyde through aldol reaction in the same reaction system. This process is called cascade halo-Michael/Aldol reaction. The cascade halo-Michael/Aldol reaction and its applications in the synthesis of related compounds according to the types of Lewis acid are introduced.
引用
收藏
页码:1608 / 1625
页数:18
相关论文
共 79 条
  • [1] EXPERIMENTS BEARING ON THE SYNTHESIS OF CORTISONE .1. SOME CYCLOPENTENONE DERIVATIVES
    ACHESON, RM
    ROBINSON, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR): : 1127 - 1133
  • [2] The reaction of porphyrins with α,β-acetylenic ketone/ester (Morita-Baylis-Hiliman) promoted by MgI2 and subsequent Sonogashira coupling reactions
    Ahmed, Naseem
    Ali, Hasrat
    van Lier, Johan E.
    [J]. JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2006, 10 (9-10) : 1172 - 1178
  • [3] Recent advances in the Baylis-Hillman reaction and applications
    Basavaiah, D
    Rao, AJ
    Satyanarayana, T
    [J]. CHEMICAL REVIEWS, 2003, 103 (03) : 811 - 891
  • [4] The Baylis-Hillman reaction: a novel concept for creativity in chemistry
    Basavaiah, Deevi
    Veeraraghavaiah, Gorre
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) : 68 - 78
  • [5] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry
    Basavaiah, Deevi
    Reddy, Bhavanam Sekhara
    Badsara, Satpal Singh
    [J]. CHEMICAL REVIEWS, 2010, 110 (09) : 5447 - 5674
  • [6] Z-Selective, Mg-mediated synthesis of α,β-unsaturated-β-iodo Morita-Baylis-Hillman-type adducts
    Bugarin, Alejandro
    Connell, Brian T.
    [J]. TETRAHEDRON LETTERS, 2015, 56 (23) : 3285 - 3287
  • [7] Enantioselective Total Synthesis of (-)-Kibdelone C
    Butler, John R.
    Wang, Chao
    Bian, Jianwei
    Ready, Joseph M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) : 9956 - 9959
  • [8] The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes by using chiral salen catalyst
    Chen, DJ
    Guo, L
    Kotti, SRSS
    Li, GG
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (10) : 1757 - 1762
  • [9] The first enantioselective halo aldol reaction of ethyl propiolate and aldehydes
    Chen, DJ
    Timmons, C
    Liu, JY
    Headley, A
    Li, GG
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) : 3330 - 3335
  • [10] SCH-47918 - A NOVEL PAF ANTAGONIST FROM THE FUNGUS PHOMA SP
    CHU, M
    PATEL, MG
    GULLO, VP
    TRUUMEES, I
    PUAR, MS
    MCPHAIL, AT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22): : 5817 - 5818