N-Oxide-Catalyzed Six-Membered Ring Bromo-Etherification of ϵ-Alkenyl Alcohols

被引：0
|
作者：
Hoshino, Yuki [1 ,2 ]
Kasahara, Honoka [1 ,2 ]
Marushima, Ryusei [1 ,2 ]
Moriyama, Katsuhiko [1 ,2 ]
机构：
[1] Chiba Univ, Grad Sch Sci, Dept Chem, 1-33 Yayoi Cho,Inage Ku, Chiba 2638522, Japan
[2] Chiba Univ, Soft Mol Activat Res Ctr, 1-33 Yayoi Cho,Inage Ku, Chiba 2638522, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2025年 / 367卷 / 02期
关键词：
Bromo-etherification; Intramolecular cyclization; N-Oxide; Organocatalyst; Tetrahydropyran; OXA-MICHAEL REACTION; NATURAL-PRODUCTS; STEREOSELECTIVE CONSTRUCTION; PRINS CYCLIZATION; TETRAHYDROPYRANS; BROMOLACTONIZATION; BROMOCYCLIZATION; BROMINATION; MACROLIDES; STRATEGIES;
D O I：
10.1002/adsc.202401209
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A six-membered ring bromo-etherification of & varepsilon;-alkenyl alcohols using an N-oxide catalyst was developed to furnish 2-bromomethyl-6-substituted tetrahydropyrans with cis-selectivity and 3-bromomethyl isochromans in high yields. DFT calculations indicate that the NMO catalyst enhances the electrophilicity of the bromine atom on NBS via two hydrogen-bonding interactions after the formation of the NMO-NBS complex.
引用
收藏
页数：7
相关论文
共 50 条
  • [1] A new silver(I) carboxylate chelate type: A six-membered ring in the N-oxide-picolinate
    Jaber, F
    Charbonnier, F
    PetitRamel, M
    Faure, R
    EUROPEAN JOURNAL OF SOLID STATE AND INORGANIC CHEMISTRY, 1996, 33 (05): : 429 - 440
  • [2] Ring Expansion of N-H Ketoaziridines to Five and Six-Membered N-Heterocycles
    Samimi, Heshmat A.
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2015, 12 (04) : 328 - 344
  • [3] Optical Properties of Chromophores with Different Six-membered N-heterocyclic Aromatic Ring
    Peng, Haitao
    Cui, Yuezhi
    Zhang, Tao
    Zhang, Yang
    Guan, Haixing
    APPLICATION OF CHEMICAL ENGINEERING, PTS 1-3, 2011, 236-238 : 1598 - 1602
  • [4] Amine-free silylation of alcohols under 4-methylpyridine N-oxide-catalyzed conditions
    Yoshida, Keisuke
    Fujino, Yuta
    Itatsu, Yukihiro
    Inoue, Hiroki
    Kanoko, Yohei
    Takao, Ken-ichi
    TETRAHEDRON LETTERS, 2016, 57 (05) : 627 - 631
  • [5] Iron-Catalyzed Synthesis of α-Dienyl Five- and Six-Membered N-Heterocycles
    Gonnard, Laurine
    Guerinot, Amandine
    Cossy, Janine
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (41) : 6160 - 6167
  • [6] Ring-opening polymerization of six-membered cyclic esters catalyzed by tetrahydroborate complexes of rare earth metals
    Nakayama, Yuushou
    Sasaki, Kenta
    Watanabe, Naoki
    Cai, Zhengguo
    Shiono, Takeshi
    POLYMER, 2009, 50 (20) : 4788 - 4793
  • [7] Synthesis and Organo-Catalyzed Ring-Opening of a Six-Membered Heterocycle Combining Phosphonate and Ester Functions
    Ungpittagul, Thasanaporn
    Virachotikul, Arnut
    Monot, Julien
    Martin-Vaca, Blanca
    Bourissou, Didier
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (04) : 733 - 739
  • [8] Ring currents in six-membered heterocycles:: the diazaborinines (CH)2B2N2
    Cernusák, I
    Fowler, PW
    Steiner, E
    MOLECULAR PHYSICS, 2000, 98 (14) : 945 - 953
  • [9] An efficient procedure for the synthesis of N-alkenyl derivatives of six-membered and larger 1,2-diaza heterocycles.
    Baccolini, G
    Munyaneza, A
    Boga, C
    TETRAHEDRON, 1996, 52 (43) : 13695 - 13702
  • [10] Efficient synthesis of six-membered ring D analogues of the pentacyclic alkaloid cephalotaxine by two palladium-catalyzed reactions
    Tietze, LF
    Schirok, H
    Wöhrmann, M
    Schrader, K
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (13) : 2433 - 2444
12345