PALLADIUM-CATALYZED SYNTHESIS OF A PHOSPHINE OXIDE WITH A CHIRAL PHOSPHORUS CENTER VIA C-H PHOSPHINATION

被引：14
|
作者：
Kuninobu, Yoichiro [1 ]
Origuchi, Kazuki [1 ]
Takai, Kazuhiko [1 ]
机构：
[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Chem & Biotechnol, Kita Ku, Okayama 7008530, Japan
来源：
HETEROCYCLES | 2012年 / 85卷 / 12期
关键词：
C-H Activation; Chiral Phosphorus Center; Palladium; Phosphination; Phosphine Oxide; LIGANDS; HYDROGENATION; CYCLIZATION;
D O I：
10.3987/COM-12-12595
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new phosphine oxide with a chiral phosphine center was synthesized from a bis(biphenyl)phosphine oxide by dehydrogenative intramolecular cyclization via P-H and C-H bond activation under palladium catalysis. The absolute configuration of one enantiomer of the phosphine oxide was determined by single crystal X-ray structure analysis. By reducing the phosphine oxide, the corresponding phosphine, which also has a chiral center, was produced. The phosphine compounds could be optically resolved by chiral HPLC column chromatography.
引用
收藏
页码：3029 / 3034
页数：6
相关论文
共 50 条
  • [1] Oxindole Synthesis via Palladium-catalyzed C-H Functionalization
    Magano, Javier
    Kiser, E. Jason
    Shine, Russell J.
    Chen, Michael H.
    Hughes, David
    ORGANIC SYNTHESES, 2013, 90 : 74 - +
  • [2] Palladium-Catalyzed Enantioselective C-H Aminocarbonylation: Synthesis of Chiral Isoquinolinones
    Han, Hui
    Zhang, Tao
    Yang, Shang-Dong
    Lan, Yu
    Xia, Ji-Bao
    ORGANIC LETTERS, 2019, 21 (06) : 1749 - 1754
  • [3] Enantioselective Synthesis of Chiral Isoindolines via Palladium-Catalyzed Asymmetric Allylic C-H Amination
    Chen, Yupeng
    Jin, Yangbin
    Li, Mingda
    Li, Jiarui
    Wu, Wanqing
    Jiang, Huanfeng
    CCS CHEMISTRY, 2024,
  • [4] Palladium-catalyzed asymmetric phosphination: Enantioselective synthesis of a P-chirogenic phosphine
    Moncarz, JR
    Laritcheva, NF
    Glueck, DS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) : 13356 - 13357
  • [5] Palladium-catalyzed enantioselective C-H functionalization via C-H palladation
    Zhan, Bei-Bei
    Jin, Liang
    Shi, Bing-Feng
    TRENDS IN CHEMISTRY, 2022, 4 (03): : 220 - 235
  • [6] Palladium-Catalyzed Synthesis of Triphenylenes via Sequential C-H Activation and Decarboxylation
    Yang, Yuzhong
    Zhou, Bang
    Zhu, Xiaoming
    Deng, Guobo
    Liang, Yun
    Yang, Yuan
    ORGANIC LETTERS, 2018, 20 (17) : 5402 - 5405
  • [7] Synthesis of Functionalized Spiroindolines via Palladium-Catalyzed Methine C-H Arylation
    Saget, Tanguy
    Perez, David
    Cramer, Nicolai
    ORGANIC LETTERS, 2013, 15 (06) : 1354 - 1357
  • [8] Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C-H activation
    Rago, Alexander J.
    Dong, Guangbin
    GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (02): : 216 - 227
  • [9] Synthesis of Isoquinolinones via Regioselective Palladium-Catalyzed C-H Activation/Annulation
    Qi, Wenke
    Wu, Yimei
    Han, Yongxu
    Li, Yi
    CATALYSTS, 2017, 7 (11)
  • [10] Total synthesis of hebispeptin A and B via palladium-catalyzed C-H arylation
    Chen, Gong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
12345