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
  • [1] Palladium-Catalyzed Asymmetric Allylic Alkylation of 4-Substituted Isoxazolidin-5-ones: Straightforward Access to β2,2-Amino Acids
    de Oliveira, Marllon Nascimento
    Arseniyadis, Stellios
    Cossy, Janine
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (19) : 4810 - 4814
  • [2] Palladium-Catalyzed Asymmetric Hydrogenation of Unprotected 3-Substituted Indoles
    Wang, Kun
    Yu, Yan-Jiang
    Wang, Xiao-Qing
    Bai, Yu-Qing
    Chen, Mu-Wang
    Zhou, Yong-Gui
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 10398 - 10407
  • [3] Palladium-catalyzed cross-coupling reactions of 4-tosyl-2(5H)-furanone with boronic acids:: A facile and efficient route to generate 4-substituted 2(5H)-furanones
    Wu, J
    Zhu, Q
    Wang, LS
    Fathi, R
    Yang, Z
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02): : 670 - 673
  • [4] Palladium-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines
    Cai, Xian-Feng
    Huang, Wen-Xue
    Chen, Zhang-Pei
    Zhou, Yong-Gui
    CHEMICAL COMMUNICATIONS, 2014, 50 (67) : 9588 - 9590
  • [5] An efficient route to 4-substituted coumarins, 2(5H)-furanones, and pyrones via palladium-catalyzed couplings of alkenyl tosylates with organoindium reagents
    Gao, Wei
    Luo, Yong
    Ding, Qiuping
    Peng, Yiyuan
    Wu, Jie
    TETRAHEDRON LETTERS, 2010, 51 (01) : 136 - 138
  • [6] Palladium-catalyzed hydrovinylation of vinyl triflates with alkynes -: An approach to the synthesis of 3-vinylfuran-2(5H)-ones
    Arcadi, A
    Cacchi, S
    Fabrizi, G
    Marinelli, F
    Pace, P
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (12) : 3305 - 3313
  • [7] Palladium-catalyzed carbonylative cyclization of 3-bromoallyl alcohols leading to furan-2(5H)-ones
    Lee, Hye Kyung
    Cho, Chan Sik
    APPLIED ORGANOMETALLIC CHEMISTRY, 2012, 26 (08) : 406 - 409
  • [8] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES .4.
    HEGEDUS, LS
    SESTRICK, MR
    MICHAELSON, ET
    HARRINGTON, PJ
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17): : 4141 - 4146
  • [9] Facile approach to 4-substituted 2(5H)-furanones
    Yao, ML
    Deng, MZ
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16): : 5034 - 5036
  • [10] Diastereoselective Palladium-Catalyzed α-Arylation of 4-Substituted Cyclohexyl Esters
    Bercot, Eric A.
    Caille, Seb
    Bostick, Tracy M.
    Ranganathan, Krishnakumar
    Jensen, Randy
    Faul, Margaret M.
    ORGANIC LETTERS, 2008, 10 (22) : 5251 - 5254