Nickel(II)-catalyzed asymmetric alkylation of acyclic oxocarbenium ions with carboxylic acid derivatives

被引：8
|
作者：
Ye, Pengbo [1 ]
Liu, Xuan [1 ]
Wang, Gang [1 ]
Liu, Lei [1 ]
机构：
[1] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2021年 / 32卷 / 03期
关键词：
Oxocarbenium ion; Acyclic; Nickel; Asymmetric catalysis; Alkylation; C-H ALKYNYLATION; ENANTIOSELECTIVE ADDITION; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION; CATALYSIS; ALDEHYDES; ACETALS; ENOLATE;
D O I：
10.1016/j.cclet.2020.08.034
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A nickel(II)-catalyzed asymmetric alkylation of acyclic oxocarbenium ions generated in situ from corresponding acetals with carboxylic acid derivatives to prepare beta-alkoxyl carbonyl moieties with diverse alpha-substituents has been disclosed. The method exhibited broad scope of acetals and carboxylic acid derivatives with excellent enantioselectivity and good functional group compatibility, and can be conducted in a gram-scale without obvious loss of efficiency. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码：1237 / 1240
页数：4
相关论文
共 50 条
  • [21] Asymmetric Construction of Acyclic 1,3-Nonadjacent Stereogenic Centers Containing a Tetrasubstituted Carbon through Diastereoselective Alkylation of Benzyl Sulfone Derivatives
    Ojima, Rihaku
    Kondoh, Azusa
    Terada, Masahiro
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [22] Nickel-catalyzed decarboxylative coupling of an alkynyl carboxylic acid with aryl iodides
    Son, Yujeong
    Kim, Han-Sung
    Lee, Ju-Hyeon
    Jang, Jisun
    Lee, Chin-Fa
    Lee, Sunwoo
    TETRAHEDRON LETTERS, 2017, 58 (14) : 1413 - 1416
  • [23] Mechanistic Aspects of Pincer Nickel(II)-Catalyzed C-H Bond Alkylation of Azoles with Alkyl Halides
    Patel, Ulhas N.
    Jain, Shailja
    Pandey, Dilip K.
    Gonnade, Rajesh G.
    Vanka, Kumar
    Punji, Benudhar
    ORGANOMETALLICS, 2018, 37 (06) : 1017 - 1025
  • [24] α-Allyl-α-aryl α-Amino Esters in the Asymmetric Synthesis of Acyclic and Cyclic Amino Acid Derivatives by Alkene Metathesis
    Curto, John M.
    Kozlowski, Marisa C.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11) : 5359 - 5364
  • [25] Iridium-Catalyzed Direct Asymmetric Alkylation of Aniline Derivatives using 2-Norbornene
    Shirai, Tomohiko
    Okamoto, Takakazu
    Yamamoto, Yasunori
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (06) : 1054 - 1056
  • [26] Nickel(II)-catalyzed enantioselective α-alkylation of β-ketoamides with phenyliodonium ylide via a radical process
    Guo, Jing
    Liu, Xiaohua
    He, Changqiang
    Tan, Fei
    Dong, Shunxi
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2018, 54 (86) : 12254 - 12257
  • [27] Nickel-Catalyzed Asymmetric Hydrovinylation Using Lewis Acid Activation
    Lassauque, Nicolas
    Francio, Giancarlo
    Leitner, Walter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (19) : 3199 - 3202
  • [28] Phase-Transfer-Catalyzed Asymmetric Michael Addition of (Iminomethyl)phosphonates to α,β-Unsaturated Ketones: Access to α-Aminophosphonic Acid Derivatives
    Li, Jin-Shan
    Cui, Han-Feng
    Zhang, Ke-Feng
    Nie, Jing
    Ma, Jun-An
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (17) : 2545 - 2552
  • [29] Diastereoselective palladium-catalyzed C(sp3)-H cyanomethylation of amino acid and carboxylic acid derivatives
    Garai, Sumit
    Ghosh, Krishna Gopal
    Biswas, Ashik
    Chowdhury, Sushobhan
    Sureshkumar, Devarajulu
    CHEMICAL COMMUNICATIONS, 2022, 58 (56) : 7793 - 7796
  • [30] Ruthenium(II)/Chiral Carboxylic Acid Catalyzed Enantioselective C-H Functionalization of Sulfoximines
    Huang, Long-Tao
    Hirata, Yuki
    Kato, Yoshimi
    Lin, Luqing
    Kojima, Masahiro
    Yoshino, Tatsuhiko
    Matsunaga, Shigeki
    SYNTHESIS-STUTTGART, 2022, 54 (21): : 4703 - 4710
12345