Insertion of Glycosylidene Carbenes into Phenolic O-H Bonds for the Synthesis of O-Aryl Glycosides

被引：0
|
作者：
Zhu, Qibin [1 ,2 ]
Tian, Xinyu [1 ,2 ]
He, Gang [1 ,2 ,3 ]
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Coll Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, Frontiers Sci Ctr New Organ Matter, Tianjin 300071, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 08期
基金：
中国国家自然科学基金;
关键词：
STEREOCONTROLLED SYNTHESIS; GLYCOSYLATION; S(N)2-GLYCOSYLATION; PRECURSORS; INHIBITORS; ARYLATION; AIR;
D O I：
10.1021/acs.joc.4c02620
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We present a new strategy for the synthesis of O-aryl glycosides through the formal insertion of glycosylidene carbenes into the O-H bond of phenols. The key glycosylidene carbene intermediates were generated in situ by copper-catalyzed oxidation of bench-stable glycosylidene diaziridine precursors. This method enables the glycosylation of a variety of phenols with good yields, excellent diastereoselectivity, and chemoselectivity, providing a highly practical method for the late-stage glycosylation of complex natural products and bioactive agents.
引用
收藏
页码：3087 / 3092
页数：6
相关论文
共 50 条
  • [1] GLYCOSYLIDENE CARBENES .2. SYNTHESIS OF O-ARYL GLYCOSIDES
    BRINER, K
    VASELLA, A
    HELVETICA CHIMICA ACTA, 1990, 73 (06) : 1764 - 1778
  • [2] Insertion of carbenes into O-H bonds of alcohols catalysed by platinum complexes
    Schils, R
    Simal, F
    Demonceau, A
    Noels, AF
    Eremenko, IL
    Sidorov, AA
    Nefedov, SE
    TETRAHEDRON LETTERS, 1998, 39 (43) : 7849 - 7852
  • [3] Silver-Catalyzed Asymmetric Insertion into Phenolic O-H Bonds using Aryl Diazoacetates and Theoretical Mechanistic Studies
    Harada, Shingo
    Tanikawa, Koki
    Homma, Haruka
    Sakai, Chigaya
    Ito, Tsubasa
    Nemoto, Tetsuhiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (52) : 12058 - 12062
  • [4] INSERTION OF METHANESULFONYLNITRENE INTO C-H AND O-H BONDS
    SHINGAKI, T
    INAGAKI, M
    TORIMOTO, N
    TAKEBAYASHI, M
    CHEMISTRY LETTERS, 1972, (12) : 1181 - 1184
  • [5] Enantioselective Carbenoid Insertion into Phenolic O-H Bonds with a Chiral Copper(I) Imidazoindolephosphine Complex
    Osako, Takao
    Panichakul, Duanghathai
    Uozumi, Yasuhiro
    ORGANIC LETTERS, 2012, 14 (01) : 194 - 197
  • [6] Synthesis of α-Peroxyesters via Organocatalyzed O-H Insertion of Hydroperoxides and Aryl Diazoesters
    Fisher, Thomas J.
    Mattson, Anita E.
    ORGANIC LETTERS, 2014, 16 (20) : 5316 - 5319
  • [7] Enantioselective Palladium-Catalyzed Insertion of α-Aryl-α-diazoacetates into the O-H Bonds of Phenols
    Xie, Xiu-Lan
    Zhu, Shou-Fei
    Guo, Jun-Xia
    Cai, Yan
    Zhou, Qi-Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (11) : 2978 - 2981
  • [8] Silver-Exchanged Zeolite Y Catalyzes a Selective Insertion of Carbenes into C-H and O-H Bonds
    Zheng, Yongkun
    Vidal-Moya, Alejandro
    Hernandez-Garrido, Juan Carlos
    Mon, Marta
    Leyva-Perez, Antonio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (45) : 24736 - 24745
  • [9] Silver-Exchanged Zeolite Y Catalyzes a Selective Insertion of Carbenes into C-H and O-H Bonds
    Zheng, Yongkun
    Vidal-Moya, Alejandro
    Hernández-Garrido, Juan Carlos
    Mon, Marta
    Leyva-Pérez, Antonio
    Journal of the American Chemical Society, 2023,
  • [10] SYNTHESIS OF O-ARYL PHOSPHONOCHLORIDOTHIONATES
    NEWALLIS, PE
    CHUPP, JP
    NUFER, HL
    JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1970, 15 (03): : 455 - &
12345