Phenyliodine diacetate-mediated oxidative cleavage of cyclobutanols leading to γ-hydroxy ketones

被引:19
|
作者
Fujioka, Hiromichi [1 ]
Komatsu, Hideyuki [1 ]
Miyoshi, Akihito [1 ]
Murai, Kenichi [1 ]
Kita, Yasuyuki [2 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
[2] Ritsumeikan Univ, Coll Pharmaceut Sci, Shiga 5258577, Japan
关键词
Cyclobutanol; Phenyliodine diacetate; Oxidation; gamma-Hydroxy ketone; HYPERVALENT IODINE OXIDATION; NUCLEOPHILIC-SUBSTITUTION; OPENING REACTION; RING; DERIVATIVES; REARRANGEMENT; ETHERS; ROUTE;
D O I
10.1016/j.tetlet.2010.12.032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidative cleavage of cyclobutanols using PIDA, which leads to efficient entry of gamma-hydroxy ketones, is described. When using 2-substituted cyclobutanols, gamma-substituted gamma-hydroxy ketones are obtained through regioselective C-C bond cleavage. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:973 / 975
页数:3
相关论文
共 31 条
  • [1] Synthesis of Oxazoles from Enamides via Phenyliodine Diacetate-Mediated Intramolecular Oxidative Cyclization
    Zheng, Yunhui
    Li, Xuming
    Ren, Chengfeng
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10353 - 10361
  • [2] Phenyliodine Diacetate-Mediated para-Functionalizations of Amido- and Amino-Substituted [2.2]Paracyclophanes
    Schaal , Petra
    Baars, Hannah
    Raabe, Gerhard
    Atodiresei, Iuliana
    Bolm, Carsten
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) : 2506 - 2512
  • [3] Oxidative β-Cleavage of Fused Cyclobutanols Leading to Hydrofuran-Fused Polycyclic Aromatic Compounds
    Kinouchi, Hayate
    Sugimoto, Kazuma
    Yamaoka, Yousuke
    Takikawa, Hiroshi
    Takasu, Kiyosei
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (18): : 12615 - 12622
  • [4] Oxidative amidation of benzyl alcohols with amino acid esters mediated by N-hydroxysuccinimide/phenyliodine diacetate
    Mahesh, Mandipogula
    Panduranga, Veladi
    Prabhu, Girish
    Kumar, Roopesh L.
    Ramana, P. Venkata
    Sureshbabu, Vommina V.
    SYNTHETIC COMMUNICATIONS, 2017, 47 (07) : 716 - 721
  • [5] Phenyliodine Diacetate-Mediated Intramolecular C(sp2)-H Amidation for 1,2-Disubstituted Benzimidazole Synthesis under Metal-Free Conditions
    Maiti, Saikat
    Mal, Prasenjit
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (07) : 1416 - 1424
  • [6] Synthesis of γ-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides
    Casey, Brian M.
    Eakin, Cynthia A.
    Flowers, Robert A., II
    TETRAHEDRON LETTERS, 2009, 50 (12) : 1264 - 1266
  • [7] Phenyliodonium Diacetate Mediated Oxidative Functionalization of Styrenes with Molecular Oxygen: Synthesis of α-Oxygenated Ketones
    Samanta, Supravat
    Donthiri, Ramachandra Reddy
    Ravi, Chitrakar
    Adimurthy, Subbarayappa
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (08): : 3457 - 3463
  • [8] Phenyliodine(III) Diacetate (PIDA) Mediated Synthesis of Aromatic Azo Compounds through Oxidative Dehydrogenative Coupling of Anilines: Scope and Mechanism
    Monir, Kamarul
    Ghosh, Monoranjan
    Mishra, Subhajit
    Majee, Adinath
    Hajra, Alakananda
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (05) : 1096 - 1102
  • [9] OXIDATIVE CLEAVAGE OF 1,2-GLYCOLS AND ALPHA-HYDROXY KETONES WITH THE JONES REAGENT
    EPIFANIO, RD
    CAMARGO, W
    PINTO, AC
    TETRAHEDRON LETTERS, 1988, 29 (49) : 6403 - 6406
  • [10] Phenyliodine(III) diacetate-mediated dearomatization of 2-(2-hydroxyaryl)benzoxazoles and 2-(2-hydroxyaryl)benzothiazoles: Regio- and stereoselective synthesis of tetramethoxycyclohexenones and bicyclo[2.2.2]octenones
    Yadav, Geeta
    Kumar, Sunil
    Kumar, Devinder
    Kataria, Ramesh
    Laroche, Christophe
    Kerwin, Sean M.
    JOURNAL OF MOLECULAR STRUCTURE, 2022, 1266