Regioselective synthesis of substituted cyclohexa-1,3-dienes via the base-mediated cyclisation of α,β-unsaturated carbonyl compounds and γ-phosphonylcrotonates

被引:2
|
作者
Joshi, Prabhakar R. [1 ]
Chandra, Rajesh [1 ]
Menon, Rajeev S. [2 ]
机构
[1] CSIR, Crop Protect Div, Indian Inst Chem Technol, Hyderabad 500007, India
[2] Cent Univ Haryana, Dept Chem, Jant Pali Mahendergarh 123031, Haryana, India
关键词
Cyclohexadiene; 3+3] benzannulation; Wadsworth Emmons reaction; Crotonates; Phosphonates; 3+3 BENZANNULATION REACTIONS; 2+2+2 CYCLOADDITION; IRREVERSIBLE INHIBITION; ACID TRANSAMINASE; 1,3-CYCLOHEXADIENE; ALDEHYDES;
D O I
10.1016/j.tetlet.2020.152380
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The base-mediated reaction of alpha,beta-unsaturated carbonyl compounds and gamma-phosphonylcrotonates under an argon atmosphere readily furnishes substituted cyclohexa-1,3-dienes. The cyclisation proceeds with complete regioselectivity to afford products that are readily amenable to further redox manipulations. The presented method allows the rapid and regioselective syntheses of six-membered carbocycles at three different oxidation levels. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数:3
相关论文
共 50 条
  • [41] Regioselective Synthesis of Substituted (3E)-1,3-Dienes from Chelated Allyl-Ironcarbene Complexes and Potassium Enoxyborates
    Boehmer, J.
    Hampel, F.
    Schobert, R.
    Synthesis, (06):
  • [42] SYNTHESIS OF 2-NITRO 1,3-DIENES - USEFUL INTERMEDIATES IN THE PREPARATION OF UNSATURATED 1,4-DICARBONYL COMPOUNDS
    BACKVALL, JE
    KARLSSON, U
    CHINCHILLA, R
    TETRAHEDRON LETTERS, 1991, 32 (40) : 5607 - 5610
  • [43] SYNTHESIS OF 4,4-DISUBSTITUTED CYCLOHEXENONES .3. THE REACTION OF 1,3-BIS(TRIMETHYLSILYLOXY)CYCLOHEXA-1,3-DIENES WITH DIENOPHILES - AN UNEXPECTED REARRANGEMENT OF THE ADDUCTS FROM THE REACTION WITH 2-CHLOROACRYLONITRILE
    CLARK, RSJ
    HOLMES, AB
    MATASSA, VG
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (05): : 1401 - 1407
  • [44] Regioselective proton abstraction and 1,3-migration of a phosphorus group in 1,3-dienes by iron coordination:: A new method for the synthesis of α-phosphono-α,β-unsaturated ketones
    Okauchi, T
    Teshima, T
    Hayashi, K
    Suetsugu, N
    Minami, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) : 12117 - 12118
  • [45] Regioselective Synthesis of Trichloromethyl-Substituted Salicylates and Cyclohexenones by One-Pot Cyclizations of 1,3-Bis(trimethylsilyloxy)buta-1,3-dienes
    Reimann, Sebastian
    Bunescu, Alina
    Petrosyan, Andranik
    Sharif, Muhammad
    Erfle, Silke
    Mamat, Constantin
    Ghochikyan, Tariel V.
    Saghyan, Ashot S.
    Spannenberg, Anke
    Villinger, Alexander
    Langer, Peter
    HELVETICA CHIMICA ACTA, 2013, 96 (10) : 1955 - 1967
  • [46] Furanose synthesis via regioselective dihydroxylation of 1-silyloxy-1,3-dienes:: Application to the furanose unit of 4-epi-hygromycin A
    Armstrong, A
    Gethin, DM
    Wheelhouse, CJ
    SYNLETT, 2004, (02) : 350 - 352
  • [47] HYDROZIRCONATION OF ALLENYLSTANNANE FOR GENERATING BIMETALLIC 3-CARBON SPECIES - SYNTHESIS OF (E)-1,3-DIENES FROM CARBONYL-COMPOUNDS
    MAETA, H
    HASEGAWA, T
    SUZUKI, K
    SYNLETT, 1993, (05) : 341 - 343
  • [48] Indium(III) halide mediated SN2′ reactions of substituted allenols:: Synthesis of 2-halo-1,3-dienes
    Cho, YS
    Jun, BK
    Pae, AN
    Cha, JH
    Koh, HY
    Chang, MH
    Han, SY
    SYNTHESIS-STUTTGART, 2004, (16): : 2620 - 2624
  • [49] STEREOSELECTIVE SYNTHESIS OF (E)-ALPHA-HYDROXY-1,3-DIENES VIA THE REACTION OF 2,5-DIHYDROTHIOPHENE S,S-DIOXIDES WITH CARBONYL-COMPOUNDS
    YAMADA, S
    SUZUKI, H
    NAITO, H
    NOMOTO, T
    TAKAYAMA, H
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (05) : 332 - 333
  • [50] BrOnsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes
    Tejo, Ciputra
    Tirtorahardjo, Davin
    Day, David Philip
    Ma, Dik-Lung
    Leung, Chung-Hang
    Chan, Philip Wai Hong
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2017, 70 (04) : 430 - 435