Recent development in asymmetric organocatalytic domino reactions involving 1,6-addition as a key step

被引:33
作者
Hussain, Yaseen [1 ]
Tamanna [1 ]
Sharma, Manisha [1 ]
Kumar, Akshay [2 ]
Chauhan, Pankaj [1 ]
机构
[1] Indian Inst Technol Jammu, Dept Chem, NH-44, Jammu 181221, Jammu & Kashmir, India
[2] DAV Univ, Dept Chem, Pathankot Jalandhar Rd, Jalandhar 144001, Punjab, India
关键词
QUINONE METHIDE DERIVATIVES; VINYLOGOUS MICHAEL ADDITION; CONJUGATE ADDITION; 1,6-CONJUGATE ADDITION; BETA-KETOESTERS; 4+2 CYCLIZATION; CASCADE; CONSTRUCTION; CATALYSIS; REMOTE;
D O I
10.1039/d1qo01561c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Due to their unique activation modes, small organic molecule catalysts (organocatalysts) have proved their potential in facilitating the remote functionalizations of unsaturated acceptors with extended conjugation. The organocatalytic 1,6-addition reaction involving the attack of nucleophiles on the delta-carbon of the alpha,beta,gamma,delta-unsaturated acceptors has emerged as an excellent strategy to create a stereocenter at the delta-site with high regio- and stereo-control. Organocatalysis has also opened the window for developing complex domino reactions involving the 1,6-addition step. Tremendous advancement has been accomplished in the organocatalytic asymmetric 1,6-addition and related domino reactions for the stereocontrolled synthesis of complex molecular structures bearing multiple stereocenters. This review article summarizes the significant advancement in stereoselective domino reactions involving 1,6-addition as a critical step.
引用
收藏
页码:572 / 592
页数:21
相关论文
共 89 条
  • [1] Adamo MFA, 2007, HETEROCYCLES, V71, P1173
  • [2] Multicomponent synthesis of spiroisoxazolines
    Adamo, MFA
    Donati, D
    Duffy, EF
    Sarti-Fantoni, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) : 8395 - 8399
  • [3] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction
    Ahrendt, KA
    Borths, CJ
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4243 - 4244
  • [4] Catalytic Asymmetric Conjugate Addition of Nitroalkanes to 4-Nitro-5-styrylisoxazoles
    Baschieri, Andrea
    Bernardi, Luca
    Ricci, Alfredo
    Suresh, Surisetti
    Adamo, Mauro F. A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) : 9342 - 9345
  • [5] Organocatalytic asymmetric 1,6-additions of β-ketoesters and glycine imine
    Bernardi, Luca
    Lopez-Cantarero, Jesus
    Niess, Barbara
    Jlrgensen, Karl Anker
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) : 5772 - 5778
  • [6] Organocatalytic Asymmetric 1,6-Addition Reactions
    Biju, Akkattu T.
    [J]. CHEMCATCHEM, 2011, 3 (12) : 1847 - 1849
  • [7] A proline-catalyzed asymmetric Robinson annulation reaction
    Bui, T
    Barbas, CF
    [J]. TETRAHEDRON LETTERS, 2000, 41 (36) : 6951 - 6954
  • [8] Synthesis of Cyclopropane Spirooxindoles by means of a Vinylogous Organocatalytic Cascade
    Cesar da Silva, Rodrigo
    Chatterjee, Indranil
    Escudero-Adan, Eduardo
    Weber Paixao, Marcio
    Melchiorre, Paolo
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (04) : 466 - 469
  • [9] Recent Progress in Organocatalytic Asymmetric Domino Transformations
    Chanda, Tanmoy
    Zhao, John C. -G.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (01) : 2 - 79
  • [10] Vinylogous Organocatalytic Triple Cascade Reaction: Forging Six Stereocenters in Complex Spiro-Oxindolic Cyclohexanes
    Chatterjee, Indranil
    Bastida, David
    Melchiorre, Paolo
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (16) : 3124 - 3130