Palladium-Catalyzed Asymmetric Hydrogenation of 4-Substituted 3-Alkoxycarbonylfuran-2(5H)-ones

被引:0
|
作者
Gao, Xuan-Yu [1 ,2 ]
Wang, Han [1 ]
Jing, Huan [1 ]
Yu, Chang-Bin [1 ]
Zhou, Yong-Gui [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
[2] Dalian Univ Technol, Sch Chem, 2 Linggong Rd, Dalian 116024, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 10期
基金
中国国家自然科学基金;
关键词
DONOR-ACCEPTOR CYCLOPROPANES; ENANTIOSELECTIVE SYNTHESIS; KETONES; REDUCTION; DIASTEREO; LIGNANS;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed asymmetric hydrogenation of tetrasubstituted olefin 4-substituted 3-alkoxycar-bonylfuran-2(5H)-ones was developed for the construction of 1,2-contiguous stereogenters, giving the chiral trans-4-substituted 3-alkoxycarbonylbutyrolactone derivatives with up to 95% of enantioselectivities. The asymmetric hydrogenation reaction could proceed smoothly at gram scale without any loss of reactivity and enantioselectivity. In addition, the synthetic utility of the chiral reductive products has been demonstrated through useful building blocks.
引用
收藏
页码:3752 / 3761
页数:10
相关论文
共 50 条
  • [21] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES .3. TOTAL SYNTHESIS OF (+/-)-AURANTIOCLAVINE
    HEGEDUS, LS
    TORO, JL
    MILES, WH
    HARRINGTON, PJ
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15): : 3319 - 3322
  • [22] Rapid access to 4-substituted-pyrones and 2(5H)-furanones via a palladium-catalyzed C-OH bond activation
    Hu, Yi
    Ding, Qiuping
    Ye, Shengqing
    Peng, Yiyuan
    Wu, Jie
    TETRAHEDRON, 2011, 67 (38) : 7258 - 7262
  • [23] Kinetic Resolution of Racemic 4-Substituted Chroman-2-ones Through Asymmetric Lactone Hydrogenation
    Wu, Xiong
    Yue, Hai-Tao
    Zuo, Xiao-Dong
    Yang, Xiao-Hui
    Yan, Pu-Cha
    Xie, Jian-Hua
    Zhou, Qi-Lin
    CCS CHEMISTRY, 2024, 6 (10): : 2560 - 2576
  • [24] Synthesis of chiral piperazin-2-ones through palladium-catalyzed asymmetric hydrogenation of pyrazin-2-ols
    Feng, Guang-Shou
    Zhao, Zi-Biao
    Shi, Lei
    Zhou, Yong-Gui
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (22): : 6273 - 6278
  • [25] 1H-Imidazol-4(5H)-ones and thiazol-4(5H)-ones as emerging pronucleophiles in asymmetric catalysis
    Mielgo, Antonia
    Palomo, Claudio
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 918 - 936
  • [26] Selective synthesis of unsymmetrical 3,4-disubstituted and 4-substituted 2(5H)-furanones
    Rossi, R
    Bellina, F
    Raugei, E
    SYNLETT, 2000, (12) : 1749 - 1752
  • [27] Simple Synthesis of Substituted 3-Hydroxyfuran-2(5H)-ones
    Lisovenko, Natalya Yu.
    Nasibullina, Ekaterina R.
    Kharitonova, Svetlana S.
    Myshkina, Olga A.
    SYNTHESIS-STUTTGART, 2021, 53 (11): : 1955 - 1961
  • [28] Synthesis of 4-alkyl-3-bromo-2(5H)-furanones and unsymmetrically disubstituted 3,4-dialkyl-2(5H)-furanones by palladium-catalyzed cross-coupling reactions
    Bellina, F
    Anselmi, C
    Rossi, R
    TETRAHEDRON LETTERS, 2001, 42 (23) : 3851 - 3854
  • [29] Palladium-catalyzed double-carbonylative cyclization of propargyl alcohols and aryl triflates to expedite construction of 4-aroyl-furan-2(5H)-ones
    Ying, Jun
    Le, Zhengjie
    Wu, Xiao-Feng
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (18): : 2757 - 2760
  • [30] Synthesis of 4-substituted imidazoles via palladium-catalyzed cross-coupling reactions
    Jetter, MC
    Reitz, AB
    SYNTHESIS-STUTTGART, 1998, (06): : 829 - 831