One-pot stereoselective synthesis of dimethyl(2-hydroxy-4,4-dimethylcyclohex-1-en-6-one-1-yl)-3-(diphenylphosphonato)butanedioate

被引:104
|
作者
Yavari, I [1 ]
Ramazani, A [1 ]
机构
[1] Tarbiat Modarres Univ, Dept Chem, Tehran, Iran
关键词
phosphonato ester; triphenyl phosphite; acetylenic ester; CH-acid; NMR spectroscopy; stereochemistry;
D O I
10.1080/10426509708033699
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Protonation of the reactive intermediate produced in the reaction between triphenyl phosphite and dimethyl acetylenedicarboxylate by 5,5-dimethylcyclohexane-1,3-dione leads to vinyltriphenoxy-phosphonium cation, which undergoes an addition reaction with the enolate anion of the CH-acid to produce the title compound in high yield.
引用
收藏
页码:73 / 77
页数:5
相关论文
共 50 条
  • [31] Synthesis, structure, and properties of piperidinium 3-(4-chlorophenyl)-2-cyano-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)thiopropionimidate
    Krivokolysko, SG
    Dyachenko, VD
    Chernega, AN
    Litvinov, VP
    RUSSIAN CHEMICAL BULLETIN, 2000, 49 (04) : 736 - 739
  • [32] Synthesis, structure, and properties of piperidinium 3-(4-chlorophenyl)-2-cyano-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)thiopropionimidate
    S. G. Krivokolysko
    V. D. Dyachenko
    A. N. Chernega
    V. P. Litvinov
    Russian Chemical Bulletin, 2000, 49 : 736 - 739
  • [33] (E)-3-(4-Chlorophenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1one
    Tang, Jie
    Chen, Jin-ying
    Jiang, Ling-qun
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : O278 - U1626
  • [34] A facile one-pot synthesis of 3-(1-Benzyl-2-phenyl-1H-imidazol-4-yl)-4-hydroxy-6-methyl-2H-pyran-2-one derivatives via multi-component approach
    Bade, Thirupaiah
    Vedula, Rajeswar Rao
    ORGANIC COMMUNICATIONS, 2014, 7 (02) : 53 - 59
  • [35] One-Pot Synthesis of 3-(2-Fluoroalkenyl)indoles
    Aldoshin, Alexander S.
    Tabolin, Andrey A.
    Ioffe, Sema L.
    Nenajdenko, Valentine G.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (27) : 4384 - 4396
  • [36] Ultrasound-assisted three-component synthesis of 3-(5-amino-1H-pyrazol-4-yl)-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)indolin-2-ones in water
    Khorrami, Afshin Rajabi
    Faraji, Fereshteh
    Bazgir, Ayoob
    ULTRASONICS SONOCHEMISTRY, 2010, 17 (03) : 587 - 591
  • [37] SYNTHESIS OF 4,4-DIMETHYL-2-NITRO-5-ALPHA-CHOLEST-1-EN-3-ONE
    MORI, T
    BANDO, H
    KANAIWA, Y
    SATO, E
    AMIYA, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1982, 30 (12) : 4516 - 4517
  • [38] 9-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3,7-trimethyl-1,2,3,4-hexahydro-9H-xanthen-1-one
    Li, YL
    Wang, XS
    Shi, DQ
    Tu, SJ
    Zhang, Y
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 : O1439 - O1441
  • [39] (E)-1-(5-Hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
    Wang, Guang-cheng
    Yang, Ying-hong
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1265 - U1692
  • [40] One-pot synthesis of the derivatives of 2-cyclopent-2-en-1-one by SOCI2/EtOH
    Hu, Zhiguo
    Dong, Zhibing
    JOURNAL OF CHEMICAL RESEARCH, 2007, (08) : 461 - 463