REACTIONS OF AN ENDOPEROXIDE WITH CHIRAL KETONES - DIASTEREOSELECTIVE FORMATION OF 1,2,4-TRIOXANES AND 1,3-DIOXOLANES

被引：18
|
作者：
JEFFORD, CW
JIN, SJ
BERNARDINELLI, G
机构：
[1] Department of Organic Chemistry, University of Geneva
来源：
TETRAHEDRON LETTERS | 1991年 / 32卷 / 49期
关键词：
Enantiodifferentiation; Peracetalization; X-ray structures;
D O I：
10.1016/0040-4039(91)80487-Q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,4-Diphenylcyclopent-2-ene 1,4-endoperoxide on catalysis with trimethylsilyl trifluoromethane-sulfonate reacted with (-)-menthone in a doubly diastereoselective manner to yield two tricyclic 1,2,4-trioxanes having the 3S,5S,6S and 3R,5R,6R configurations respectively. The corresponding pair of 1,3-dioxolanes arising by Baeyer-Villiger-type rearrangement was also formed.
引用
收藏
页码：7243 / 7246
页数：4
相关论文
共 50 条
  • [31] Potent Antimalarial 1,2,4-Trioxanes through Perhydrolysis of Epoxides
    Hao, Hong-Dong
    Wittlin, Sergio
    Wu, Yikang
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (23) : 7605 - 7619
  • [32] REACTION OF SINGLET OXYGEN WITH ENOL ETHERS IN THE PRESENCE OF ACETALDEHYDE - FORMATION OF 1,2,4-TRIOXANES
    JEFFORD, CW
    KOHMOTO, S
    BOUKOUVALAS, J
    BURGER, U
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (21) : 6498 - 6499
  • [33] Orally active amino functionalized antimalarial 1,2,4-trioxanes
    Singh, C
    Malik, H
    Puri, SK
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) : 459 - 462
  • [34] The photo-oxygenation of dihydropyrans. Formation of 1,2-dioxetanes and 1,2,4-trioxanes
    Jefford, CW
    Deheza, MF
    Wang, JB
    HETEROCYCLES, 1997, 46 : 451 - 462
  • [35] PHOTOOXYGENATION OF INDENE AND 1,2-DIHYDRONAPHTHALENE - FORMATION OF 1,2-DIOXETANES AND 1,2,4-TRIOXANES
    JEFFORD, CW
    HATSUI, T
    DEHEZA, MF
    BERNARDINELLI, G
    CHIMIA, 1992, 46 (04) : 114 - 118
  • [36] Synthesis of Fatty 1,2,4-Trioxanes by Peracetalization of β-Hydroxy Hydroperoxides
    Miguel, Thomas De Dios
    Louvel, Dan
    Onida, Killian
    Lavoignat, Adeline
    Picot, Stephane
    Duguet, Nicolas
    SYNTHESIS-STUTTGART, 2022, 54 (03): : 617 - 628
  • [37] Versatility of the cyclo-oxymercuriation route to 1,2,4-trioxanes
    Bloodworth, A. J.
    Hagen, T.
    Johnson, K. A.
    LeNoir, I.
    Tetrahedron Letters, 38 (04):
  • [38] Copper(II)-catalyzed formation of 1,3-dioxolanes from oxiranes
    Lee, SH
    Lee, JC
    Li, MX
    Kim, NS
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2005, 26 (02) : 221 - 222
  • [39] Interaction of 2-Monosubstituted 1,3-Dioxolanes with Aluminacyclopentanes
    T. F. Dekhtyar’
    O. S. Vostrikova
    S. S. Zlotskii
    A. A. Bogomazova
    N. N. Mikhailova
    Petroleum Chemistry, 2019, 59 : 650 - 655
  • [40] Mechanistic perspectives for 1,2,4-trioxanes in anti-cancer therapy
    Efferth, T
    DRUG RESISTANCE UPDATES, 2005, 8 (1-2) : 85 - 97
12345