Enantioselective Construction of Quaternary Carbon Stereocenter via Palladium-Catalyzed Asymmetric Allylic Alkylation of Lactones

被引:23
|
作者
Li, Xiao-Hui [1 ]
Wan, Shi-Li [1 ]
Chen, Di [1 ]
Liu, Qing Rong [1 ]
Ding, Chang-Hua [1 ]
Fang, Ping [1 ]
Hou, Xue-Long [1 ,2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 10期
基金
中国国家自然科学基金;
关键词
palladium; allylic alkylation; asymmetric catalysis; lactones; quaternarycarbon; KINETIC RESOLUTION; ACYCLIC KETONES; ALLYLATION; REGIO; SUBSTITUTION; LIGANDS; AMINATION; DIASTEREO; ESTERS;
D O I
10.1055/s-0035-1561574
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and practical method for the synthesis of ,-disubstituted six-membered lactones was developed. Enantioselective construction of quaternary carbon centers by utilizing Pd-catalyzed asymmetric allylic alkylation proved its feasibility.
引用
收藏
页码:1568 / 1572
页数:5
相关论文
共 50 条
  • [31] Efficient palladium-catalyzed asymmetric allylic alkylation of ketones and aldehydes
    Zhao, Xiaohu
    Liu, Delong
    Xie, Fang
    Liu, Yangang
    Zhang, Wanbin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (06) : 1871 - 1875
  • [32] Enamines: efficient nucleophiles for the palladium-catalyzed asymmetric allylic alkylation
    Zhao, Xiaohu
    Liu, Delong
    Xie, Fang
    Zhang, Wanbin
    TETRAHEDRON, 2009, 65 (02) : 512 - 517
  • [33] Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Enol Carbonates
    Trost, Barry M.
    Xu, Jiayi
    Schmidt, Thomas
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (51) : 18343 - 18357
  • [34] Chiral sulfideoxathiane ligands for palladium-catalyzed asymmetric allylic alkylation
    Okuyama, Y
    Nakano, H
    Saito, Y
    Takahashi, K
    Hongo, H
    TETRAHEDRON-ASYMMETRY, 2005, 16 (15) : 2551 - 2557
  • [35] Palladium-catalyzed asymmetric allylic alkylation with an enamine as the nucleophilic reagent
    Liu, Delong
    Xie, Fang
    Zhang, Wanbin
    TETRAHEDRON LETTERS, 2007, 48 (43) : 7591 - 7594
  • [36] Enantioselective palladium-catalyzed allylic substitutions with asymmetric chiral ligands
    Helmchen, G
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 203 - 214
  • [37] Asymmetric construction of quaternary carbon stereocenter by Pd-hemilabile ligand-catalyzed allylic substitution
    Fukuda, Yoshimasa
    Kondo, Kazuhiro
    Aoyama, Toyohiko
    TETRAHEDRON LETTERS, 2007, 48 (19) : 3389 - 3391
  • [38] Application of chiral dipyridylmethane ligands in the enantioselective palladium-catalyzed allylic alkylation
    Chelucci, G
    Chessa, S
    Orrù, G
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 220 (02) : 145 - 151
  • [39] Mechanistic analysis of a palladium-catalyzed enantioselective decarboxylative allylic alkylation reaction
    Sargent, Andrew
    Morehead, Andrew
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [40] Palladium-Catalyzed Enantioselective Desymmetrization of Silacyclobutanes: Construction of Silacycles Possessing a Tetraorganosilicon Stereocenter
    Shintani, Ryo
    Moriya, Kohei
    Hayashi, Tamio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (41) : 16440 - 16443