Cycloadditions of Allylsilanes - Part 22. Stereoselective Synthesis of Cyclopentanes and Cyclobutanes by Lewis Acid Promoted [3+2] and [2+2] Cycloadditions of Allylsilanes

被引：34
|
作者：
Schmidt, Arndt W. [1 ]
Knoelker, Hans-Joachim [1 ]
机构：
[1] Tech Univ Dresden, Dept Chem, D-01069 Dresden, Germany
来源：
SYNLETT | 2010年 / 15期
关键词：
annulations; cycloadditions; enones; Lewis acids; silicon; STEREOCONTROLLED TOTAL-SYNTHESIS; OPTICALLY-ACTIVE ALLYLSILANES; OCCURRING TERPENE DERIVATIVES; HYDROGEN-PEROXIDE OXIDATION; TRANSITION-METAL-COMPLEXES; SCALE ASPIDIOTUS-NERII; ORGANIC-SYNTHESIS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; ABSOLUTE-CONFIGURATION;
D O I：
10.1055/s-0030-1258549
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of Lewis acid promoted [3+2] and [2+2] cycloadditions as a novel methodology for the stereoselective construction of cyclopentanes and cyclobutanes is described. Elegant applications of this methodology to the total synthesis of biologically active terpenoid natural products are presented.
引用
收藏
页码：2207 / 2239
页数：33
相关论文
共 50 条
  • [1] Cycloadditions of allylsilanes, part 11. Stereoselective synthesis of hydroxycyclopentanes and hydroxymethylcyclobutanes by titanium tetrachloride-promoted [3+2] and [2+2] cycloadditions of sterically hindered allylsilanes and subsequent oxidative cleavage of the carbon-silicon bond
    Knolker, HJ
    Jones, PG
    Wanzl, G
    SYNLETT, 1998, (06) : 613 - +
  • [2] Lewis Acid-Promoted Ketene-Alkene [2+2] Cycloadditions
    Rasik, Christopher M.
    Brown, M. Kevin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (05) : 1673 - 1676
  • [3] Lewis acid-promoted [2+2] cycloadditions of alkenes with aryl ketenes
    Rigsbee, E. M.
    Zhou, C.
    Rasik, C. M.
    Spitz, A. Z.
    Nichols, A. J.
    Brown, M. K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (24) : 5477 - 5480
  • [4] Intermolecular Ketene-Alkene [2+2] Cycloadditions: The Significance of Lewis Acid Promoted Variants
    Rasik, Christopher M.
    Brown, M. Kevin
    SYNLETT, 2014, 25 (06) : 760 - 765
  • [5] Stereoselective Lewis Acid Mediated (3+2) Cycloadditions of N-H- and N-Sulfonylaziridines with Heterocumulenes
    Craig, Robert A., II
    O'Connor, Nicholas R.
    Goldberg, Alexander F. G.
    Stoltz, Brian M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (16) : 4806 - 4813
  • [6] Highly stereoselective synthesis of bicyclo[n.3.0]alkanes by titanium tetrachloride promoted [3+2] cycloaddition of allylsilanes and 1-acetylcycloalkenes
    Knolker, HJ
    Foitzik, N
    Goesmann, H
    Graf, R
    Jones, PG
    Wanzl, G
    CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (04) : 538 - 551
  • [7] Catalytic Asymmetric [3+2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles
    Hanhan, Nadine V.
    Ball-Jones, Nicolas R.
    Tran, Ngon T.
    Franz, Annaliese K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 989 - 992
  • [8] Stereoselective [2+2]-Cycloadditions of chiral allenic ketones and alkenes: Applications towards the synthesis of benzocyclobutenes and endiandric acids
    Guo, Renyu
    Witherspoon, Brittany P.
    Brown, M. Kevin
    TETRAHEDRON, 2022, 122
  • [9] Stereoselective Construction of 1,3-Disilylcyclopentane Derivatives by Scandium-Catalyzed [3+2] Cycloaddition of Allylsilanes to β-Silylenones
    Okamoto, Kazuhiro
    Tamura, Eisuke
    Ohe, Kouichi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) : 10195 - 10199
  • [10] Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes
    Mloston, Grzegorz
    Kowalczyk, Mateusz
    Augustin, Andre U.
    Jones, Peter G.
    Werz, Daniel B.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (46) : 6250 - 6253
12345