Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions

被引:0
作者
Qin Hao [1 ]
Hou Chuanjin [1 ,2 ]
Liang Dinghua [1 ]
He Xinwei [2 ]
Li Ling [1 ,3 ]
Hu Xiangping [3 ]
机构
[1] Dalian Polytech Univ, Sch Light Ind & Chem Engn, Dalian 116034, Liaoning, Peoples R China
[2] Anhui Normal Univ, Key Lab Funct Mol Solids, Minist Educ, Wuhu 241000, Anhui, Peoples R China
[3] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Liaoning, Peoples R China
关键词
P; N; N-ligands; asymmetric allylic substitution; palladium; FORMAL 3+2 CYCLOADDITION; DECARBOXYLATIVE PROPARGYLIC ALKYLATION; ENANTIOSELECTIVE SYNTHESIS; IRIDIUM CATALYSTS; BETA-KETOESTERS; VICINAL TERTIARY; EFFICIENT ACCESS; HYDROGENATION; ESTERS; DEAROMATIZATION;
D O I
10.6023/cjoc202306004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral P,N,N-ligands are a new type of ligands developed in recent years, which have been widely used in asymmetric catalytic reactions. In this study, chiral P,N,N-ligands were applied to palladium-catalyzed asymmetric allylic substitution reactions. The results showed that under mild conditions, various nucleophiles containing carbon, nitrogen and oxygen could react smoothly, achieving good yields (up to 97% yield) and enantioselectivities (up to 93% ee).
引用
收藏
页码:282 / 290
页数:9
相关论文
共 85 条
  • [21] Regio- and Enantioselective Allylic Alkylation of Terminal Alkynes by Synergistic Rh/Cu Catalysis
    Huang, Wen-Yu
    Lu, Chun-Hua
    Ghorai, Samir
    Li, Bing
    Li, Changkun
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (36) : 15276 - 15281
  • [22] Copper-Catalyzed Enantioconvergent Radical Suzuki-Miyaura C(sp3)-C(sp2) Cross-Coupling
    Jiang, Sheng-Peng
    Dong, Xiao-Yang
    Gu, Qiang-Shuai
    Ye, Liu
    Li, Zhong-Liang
    Liu, Xin-Yuan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (46) : 19652 - 19659
  • [23] Synthesis of γ-Lactams and γ-Lactones via Intramolecular Pd-Catalyzed Allylic Alkylations
    Kammerer, Claire
    Prestat, Guillaume
    Madec, David
    Poli, Giovanni
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) : 3439 - 3447
  • [24] The Enantioselective Synthesis of Chiral Carbocyclic Nucleosides via Palladium-Catalyzed Asymmetric Allylic Amination of Alicyclic MBH Adducts with Purines
    Kang, Bo
    Zhang, Qi-Ying
    Qu, Gui-Rong
    Guo, Hai-Ming
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (10) : 1955 - 1960
  • [25] Enantioselective Allylic Amination of Trifluoromethyl Group Substituted Racemic and Unsymmetrical 1,3-Disubstituted Allylic Esters by Palladium Catalysts
    Kawatsura, Motoi
    Terasaki, Shou
    Minakawa, Maki
    Hirakawa, Takuya
    Ikeda, Kazunori
    Itoh, Toshiyuki
    [J]. ORGANIC LETTERS, 2014, 16 (09) : 2442 - 2445
  • [26] Palladium-(S,pR)-ferro NPS-catalyzed asymmetric allylic etherification:: Electronic effect of nonconjugated substituents on benzylic alcohols on enantioselectivity
    Lam, Fuk Loi
    Au-Yeung, Terry Tin-Lok
    Kwong, Fuk Yee
    Zhou, Zhongyuan
    Wong, Kwok Yin
    Chan, Albert S. C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (07) : 1280 - 1283
  • [27] Rh-Catalyzed Regio- and Enantioselective Allylic Phosphinylation
    Li, Bing
    Liu, Min
    Rehman, Sajid Ur
    Li, Changkun
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (07) : 2893 - 2898
  • [28] Copper-catalyzed propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones: enantioselective access to optically active dihydropyrano[2,3-c]pyrazoles
    Li, Ling
    Liu, Zhen-Ting
    Hu, Xiang-Ping
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (85) : 12033 - 12036
  • [29] Preparation and Application of Amino Phosphine Ligands Bearing Spiro[indane-1,2′-pyrrolidine] Backbone
    Li, Shasha
    Zhang, Jinxia
    Li, Hongjie
    Feng, Lifei
    Jiao, Peng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (15) : 9460 - 9473
  • [30] Palladium-Catalyzed Asymmetric Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters by Allylation of β-Ketocarbonyls with Morita-Baylis-Hillman Adducts
    Liu, Jiawang
    Han, Zhaobin
    Wang, Xiaoming
    Meng, Fanye
    Wang, Zheng
    Ding, Kuiling
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (18) : 5050 - 5054