IBS-Catalyzed Oxidative Rearrangement of Tertiary Allylic Alcohols to Enones with Oxone

被引：75
作者：
Uyanik, Muhammet [1 ]
Fukatsu, Ryota [1 ]
Ishihara, Kazuaki [1 ]
机构：
[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 15期
关键词：
HYPERVALENT IODINE REAGENTS; 2-IODOXYBENZENESULFONIC ACID; POLYVALENT IODINE; TRANSPOSITION; ROUTE; CYCLOPENTENONES; ALKALOIDS; CHEMISTRY; ALDEHYDES; PHENOLS;
D O I：
10.1021/ol9013188
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A 2-iodoxybenzenesulfonic acid (IBS)-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with powdered Oxone in the presence of potassium carbonate and tetrabutylammonium hydrogen sulfate has been developed.
引用
收藏
页码：3470 / 3473
页数：4
相关论文
共 48 条
  • [1] Aggarwal V. K., 2003, J AM CHEM SOC, V125, P4229
  • [2] 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
  • [3] A new entry to Amaryllidaceae alkaloids from carbohydrates:: total synthesis of (+)-vittatine
    Bohno, M
    Imase, H
    Chida, N
    [J]. CHEMICAL COMMUNICATIONS, 2004, (09) : 1086 - 1087
  • [4] TRANSPOSITION OF ALLYLIC ALCOHOLS CONTROLLED BY THE PH2PO GROUP - REAGENTS FOR ALPHA-HYDROXY-DIENE SYNTHESIS BY THE HORNER-WITTIG REACTION
    BROWN, PS
    MCELROY, AB
    WARREN, S
    [J]. TETRAHEDRON LETTERS, 1985, 26 (02) : 249 - 252
  • [5] NEW SYNTHESIS OF CYCLOPENTENONES - METHYL JASMONATE AND JASMONE
    BUCHI, G
    EGGER, B
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (14) : 2021 - &
  • [6] First enantiospecific synthesis of (-)-parvifoline and (-)-curcuquinone
    Chavan, Subhash P.
    Thakkar, Mahesh
    Jogdand, Ganesh F.
    Kalkote, Uttam R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23) : 8986 - 8988
  • [7] Oxidative amidation of phenols through the use of hypervalent iodine reagents: Development and applications
    Ciufolini, Marco A.
    Braun, Norbert A.
    Canesi, Sylvain
    Ousmer, Malika
    Chang, Jonah
    Chai, David
    [J]. SYNTHESIS-STUTTGART, 2007, (24): : 3759 - 3772
  • [8] 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
  • [9] CATALYTIC EPOXIDATION OF ALKENES WITH OXONE
    DENMARK, SE
    FORBES, DC
    HAYS, DS
    DEPUE, JS
    WILDE, RG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) : 1391 - 1407
  • [10] Hypervalent iodine reagents as a new entrance to organocatalysts
    Dohi, Toshifumi
    Kita, Yasuyuki
    [J]. CHEMICAL COMMUNICATIONS, 2009, (16) : 2073 - 2085
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