Pd(II)-catalyzed aliphatic Claisen rearrangements of acyclic allyl vinyl ethers

被引：20
|
作者：
Kerrigan, Nessan J. [1 ]
Bungard, Christopher J. [1 ]
Nelson, Scott G. [1 ]
机构：
[1] Univ Pittsburgh, Dept Chem, Ctr Chem Methodol & Lib Dev, Pittsburgh, PA 15260 USA
来源：
TETRAHEDRON | 2008年 / 64卷 / 29期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
D O I：
10.1016/j.tet.2008.04.056
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium (II)-catalyzed [3,3] sigmatropic rearrangement of acyclic allyl vinyl ethers delivers 2,3-anti disubstituted pentenal Claisen adducts with high diastereoselectivity. Reaction conditions for circumventing allyl vinyl ether cleavage that had previously plagued catalyzed rearrangement of alpha-unsubstituted vinyl ether substrates are described. Merging Pd(II) catalysis with the facile access to the Claisen substrates afforded by Ir(I)-catalyzed olefin isomerization provides an expedient procedure for realizing asymmetric anti-selective Claisen rearrangements. (C) 2008 Elsevier Ltd. All Fights reserved.
引用
收藏
页码：6863 / 6869
页数：7
相关论文
共 50 条
  • [1] Catalyzed olefin isomerization leading to highly stereoselective Claisen rearrangements of aliphatic allyl vinyl ethers
    Nelson, SG
    Bungard, CJ
    Wang, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (43) : 13000 - 13001
  • [2] PALLADIUM(II)-CATALYZED CLAISEN REARRANGEMENT OF ALLYL VINYL ETHERS
    VANDERBAAN, JL
    BICKELHAUPT, F
    TETRAHEDRON LETTERS, 1986, 27 (51) : 6267 - 6270
  • [3] Catalysis of the Claisen rearrangement of aliphatic allyl vinyl ethers
    Hiersemann, M
    Abraham, L
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (09) : 1461 - 1471
  • [4] Claisen rearrangement of aliphatic allyl vinyl ethers in the presence of copper(II) bisoxazoline
    Balta, Buelent
    Ozturk, Cem
    Aviyente, Viktorya
    Vincent, Mark A.
    Hillier, Ian H.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13): : 4800 - 4809
  • [5] The Pd(II)-catalyzed and the thermal Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers
    Hiersemann, M
    SYNLETT, 1999, (11) : 1823 - 1825
  • [6] Claisen Rearrangements of Benzyl Vinyl Ethers and Heterobenzyl Vinyl Ethers
    Burns, Jed M.
    Krenske, Elizabeth H.
    McGeary, Ross P.
    SYNTHESIS-STUTTGART, 2018, 50 (09): : 1750 - 1772
  • [7] REDUCTIVE CLAISEN REARRANGEMENTS OF ANTHRAQUINONE ALLYL ETHERS
    BODDY, IK
    BONIFACE, PJ
    CAMBIE, RC
    CRAW, PA
    LARSEN, DS
    MCDONALD, H
    RUTLEDGE, PS
    WOODGATE, PD
    TETRAHEDRON LETTERS, 1982, 23 (42) : 4407 - 4408
  • [8] MECHANISM OF THE CLAISEN REARRANGEMENT OF ALLYL VINYL ETHERS
    DEWAR, MJS
    JIE, CX
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) : 511 - 519
  • [9] Iodine-Catalyzed Claisen-Rearrangements of Allyl Aryl Ethers and Subsequent Iodocyclizations
    Arndt, Thiemo
    Raina, Abhinav
    Breugst, Martin
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (05)
  • [10] STUDIES ON THE ADDITION OF ALLYL OXIDES TO SULFONYLALLENES - PREPARATION OF HIGHLY SUBSTITUTED ALLYL VINYL ETHERS FOR CARBANIONIC CLAISEN REARRANGEMENTS
    DENMARK, SE
    HARMATA, MA
    WHITE, KS
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18): : 4031 - 4042
12345