BINOL-derived bifunctional sulfide catalysts for asymmetric synthesis of 3,3-disubstituted phthalides via bromolactonization

被引:0
|
作者
Okada M. [1 ]
Kaneko K. [2 ]
Yamanaka M. [2 ]
Shirakawa S. [1 ]
机构
[1] Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki
[2] Department of Chemistry and Research Center for Smart Molecules, Faculty of Science, Rikkyo University, 3-34-1 Nishi-Ikebukuro Toshima-ku, Tokyo
来源
Organic and Biomolecular Chemistry | 2019年 / 17卷 / 15期
基金
日本学术振兴会;
关键词
D O I
10.1039/C9OB00417C
中图分类号
学科分类号
摘要
An efficient enantioselective synthesis of 3,3-disubstituted phthalides possessing a chiral quaternary carbon center was achieved via catalytic asymmetric bromolactonization that utilized BINOL-derived bifunctional sulfide catalysts. Transformations of the bromo group in optically active phthalide products were also performed to demonstrate the utility of this novel synthetic protocol. © The Royal Society of Chemistry.
引用
收藏
页码:3747 / 3751
页数:4
相关论文
共 50 条
  • [21] Organocatalytic asymmetric synthesis of 3,3-disubstituted oxindoles featuring two heteroatoms at the C3 position
    Zhou, Feng
    Zeng, Xing-Ping
    Wang, Chao
    Zhao, Xiao-Li
    Zhou, Jian
    CHEMICAL COMMUNICATIONS, 2013, 49 (20) : 2022 - 2024
  • [22] Asymmetric Synthesis of γ-Lactones Bearing α,γ-Bis-Quaternary Stereocenters via Chiral Bifunctional Sulfide-Catalyzed Desymmetrizing Bromolactonization
    Furuya, Yasuaki
    Nishiyori, Ryuichi
    Okuno, Ken
    Mori, Taiki
    Sumida, Sao
    Yamakawa, Mina
    Shirakawa, Seiji
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [23] Critical Ligand and Salt Effects in Organomagnesiate-Promoted 3,3-Disubstituted Phthalides Synthesis from 2-Iodobenzoate Derivatives
    Touchet, Sabrina
    Yeardley, Callum
    O'Hara, Charles T.
    Gros, Philippe C.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (34) : 4835 - 4845
  • [24] Synthesis of Chiral 3,3ʹ-Disubstituted (S)-BINOL Derivatives via the Kumada and Suzuki Coupling and Their Antibacterial Activity
    A. Reddy Ankireddy
    K. Paidikondala
    R. Syed
    R. Gundla
    Ch. Venkata Ramana Reddy
    T. Ganapathi
    Russian Journal of General Chemistry, 2020, 90 : 1507 - 1517
  • [25] Rhodium-catalyzed asymmetric one-pot transesterification and [2+2+2] cycloaddition leading to enantioenriched 3,3-disubstituted phthalides
    Tanaka, Ken
    Osaka, Takuya
    Noguchi, Keiichi
    Hirano, Masao
    ORGANIC LETTERS, 2007, 9 (07) : 1307 - 1310
  • [26] Asymmetric synthesis of propargylamides via 3,3′-disubstituted binaphthol-modified alkynylboronates
    Wu, TR
    Chong, JM
    ORGANIC LETTERS, 2006, 8 (01) : 15 - 18
  • [27] Synthesis of 3,3-disubstituted allyl isoindolinones via Pd-catalyzed decarboxylative allylic alkylation
    Alvarado, Mario
    Loo, Marisa
    Adler, Hanna
    Arnall, Caroline
    Amsden, Katharine
    Martinez, Gisela
    Navarro, Raul
    TETRAHEDRON LETTERS, 2024, 148
  • [28] Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams
    Amat, Mercedes
    Lozano, Oscar
    Escolano, Carmen
    Molins, Elies
    Bosch, Joan
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12): : 4431 - 4439
  • [29] The remarkable effect of the 7-substituent in the diastereoselective oxidative rearrangement of indoles: Asymmetric synthesis of 3,3-disubstituted oxindoles
    Lachia, Mathilde
    Poriel, Cyril
    Slawin, Alexandra M. Z.
    Moody, Christopher J.
    CHEMICAL COMMUNICATIONS, 2007, (03) : 286 - 288
  • [30] One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes
    Maslivetc, Vladimir A.
    Rubina, Marina
    Rubin, Michael
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (34) : 8993 - 8995