A one-pot oxidation/allylation/oxidation sequence for the preparation of β,γ-unsaturated ketones directly from primary alcohols

被引：9
作者：
Moody, Catherine L. [1 ]
Pugh, David S. [1 ]
Taylor, Richard J. K. [1 ]
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 19期
基金：
英国工程与自然科学研究理事会;
关键词：
Oxidation; Allylation; beta; gamma-Unsaturated ketones; alpha; beta-Unsaturated ketones; CONVENIENT SYNTHESIS; ALLYLATION; ALDEHYDES;
D O I：
10.1016/j.tetlet.2011.03.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot oxidation/allylation/oxidation procedure has been developed for the conversion of primary alcohols into beta,gamma-unsaturated ketones. The methodology has been applied to a range of alcohols, and in some cases, isomerisation to produce the corresponding alpha,beta-unsaturated ketones has been carried out. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2511 / 2514
页数：4
相关论文
共 21 条
  • [1] [Anonymous], MODERN CARBONYL CHEM
  • [2] YTTERBIUM TRIFLUOROMETHANESULFONATE [YB(OTF)(3)] AS A NOVEL CATALYST FOR THE ALLYLATION OF ALDEHYDES
    ASPINALL, HC
    BROWNING, AF
    GREEVES, N
    RAVENSCROFT, P
    [J]. TETRAHEDRON LETTERS, 1994, 35 (26) : 4639 - 4640
  • [3] Potassium allyl- and crotyltrifluoroborates: Stable and efficient agents for allylation and crotylation
    Batey, RA
    Thadani, AN
    Smil, DV
    [J]. TETRAHEDRON LETTERS, 1999, 40 (23) : 4289 - 4292
  • [4] A convenient preparation of (E)-3-penten-2-one
    Chiu, P
    Wong, ST
    [J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (24) : 4513 - 4516
  • [5] Denmark S. E., 2000, MODERN CARBONYL CHEM
  • [6] Enantioselective reduction of heteroaromatic β,γ-unsaturated ketones as an alternative to allylboration of aldehydes.: Application:: asymmetric synthesis of SIB-1508Y
    Felpin, FX
    Bertrand, MJ
    Lebreton, J
    [J]. TETRAHEDRON, 2002, 58 (37) : 7381 - 7389
  • [7] Ytterbium mediated coupling of α-oxonitriles with allylbromides:: convenient synthesis of β,γ-unsaturated ketones
    Gohain, M
    Gogoi, BJ
    Prajapati, D
    Sandhu, JS
    [J]. NEW JOURNAL OF CHEMISTRY, 2003, 27 (07) : 1038 - 1040
  • [8] Pd-catalyzed carboetherification of β,γ-unsaturated oximes:: A novel approach to Δ2-isoxazolines
    Jiang, Dahong
    Peng, Jinsong
    Chen, Yuanwei
    [J]. ORGANIC LETTERS, 2008, 10 (09) : 1695 - 1698
  • [9] Preparation and reactions of masked allylic organozinc reagents
    Jones, P
    Knochel, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) : 186 - 195
  • [10] Katritzky A. R., 2005, COMPREHENSIVE ORGANI
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