Expanding the scope of the Babler-Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols

被引：5
作者：
Killoran, Patrick M. [1 ]
Rossington, Steven B. [1 ]
Wilkinson, James A. [1 ]
Hadfield, John A. [1 ]
机构：
[1] Univ Salford, Kidscan Labs, Biomed Res Ctr, Salford M5 4WT, Lancs, England
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 35期
关键词：
Allylic rearrangement; Oxidative transposition; Stereoselective; Chromium; Co-oxidant; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; CYCLOADDITION; REARRANGEMENT; ALDEHYDES; ROUTE;
D O I：
10.1016/j.tetlet.2016.07.076
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report the catalytic chromium-mediated oxidation of secondary allylic alcohols to give alpha,beta-unsaturated aldehydes with exclusive (E)-stereoselectivity. This facile procedure employs catalytic PCC (5 mol %) and periodic acid (H5IO6) as a co-oxidant. This transformation occurs specifically with aromatic substituted allyl alcohols containing both electron withdrawing and electron donating substituents as well as a range of functional groups. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3954 / 3957
页数：4
相关论文
共 33 条
  • [1] FACILE METHOD FOR BIS-HOMOLOGATION OF KETONES TO ALPHA,BETA-UNSATURATED ALDEHYDES - APPLICATION TO SYNTHESIS OF CYCLOHEXANOID COMPONENTS OF BOLL-WEEVIL SEX ATTRACTANT
    BABLER, JH
    COGHLAN, MJ
    [J]. SYNTHETIC COMMUNICATIONS, 1976, 6 (07) : 469 - 474
  • [2] Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans
    Bateman, T. David
    Joshi, Aarti L.
    Moon, Kwangyul
    Galitovskaya, Elena N.
    Upreti, Meenakshi
    Chambers, Timothy C.
    McIntosh, Matthias C.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (24) : 6898 - 6901
  • [3] RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS
    BOWDEN, K
    HEILBRON, IM
    JONES, ERH
    WEEDON, BCL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN): : 39 - 45
  • [4] NEW SYNTHESIS OF CYCLOPENTENONES - METHYL JASMONATE AND JASMONE
    BUCHI, G
    EGGER, B
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (14) : 2021 - &
  • [5] DIRECT OXIDATION OF TERTIARY ALLYLIC ALCOHOLS - SIMPLE AND EFFECTIVE METHOD FOR ALKYLATIVE CARBONYL TRANSPOSITION
    DAUBEN, WG
    MICHNO, DM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) : 682 - 685
  • [6] Organoselenium-Catalyzed, Hydroxy-Controlled Regio- and Stereoselective Amination of Terminal Alkenes: Efficient Synthesis of 3-Amino Allylic Alcohols
    Deng, Zhimin
    Wei, Jialiang
    Liao, Lihao
    Huang, Haiyan
    Zhao, Xiaodan
    [J]. ORGANIC LETTERS, 2015, 17 (08) : 1834 - 1837
  • [7] A catalytic Michael addition of thiols to α,β-unsaturated carbonyl compounds:: Asymmetric Michael additions and asymmetric protonations
    Emori, E
    Arai, T
    Sasai, H
    Shibasaki, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) : 4043 - 4044
  • [8] Iminium catalysis
    Erkkila, Anniina
    Majander, Inkeri
    Pihko, Petri M.
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5416 - 5470
  • [9] Gademann K, 2002, ANGEW CHEM, V114, P3185
  • [10] Novel rhenium(I) catalysts for the isomerization of propargylic alcohols into α,β-unsaturated carbonyl compounds: an unprecedented recyclable catalytic system in ionic liquids
    Garcia-Alvarez, Joaquin
    Diez, Josefina
    Gimeno, Jose
    Seifried, Christine M.
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (22) : 6470 - 6472
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