Rhodium-Catalyzed Regio- and Enantioselective Direct Allylation of Methyl Ketones

被引：2
|
作者：
Li, Bing [1 ]
Li, Changkun [1 ]
机构：
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
来源：
SYNLETT | 2022年 / 33卷 / 18期
基金：
中国国家自然科学基金;
关键词：
rhodium catalysis; bisoxazolinephosphines; ketones; allylic substitution; asymmetric catalysis; ASYMMETRIC ALLYLIC ALKYLATION; 2,4-DISUBSTITUTED CYCLOPENTENONES; EQUILIBRIUM ACIDITIES; DUAL CATALYSIS; ENANTIO; DIASTEREO; ACETATES; LIGANDS;
D O I：
10.1055/a-1892-4134
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a highly branch-selective and enantioselective allylic alkylation of simple ketones with racemic aliphatic allylic carbonates under mild conditions. By using a Rh-bisoxazolinephosphine system and catalytic amounts of a base in THF, a series of chiral beta-branched gamma,delta-unsaturated ketones were obtained with excellent regio- and enantioselectivities. An outer-sphere nucleophilic substitution C-C bond-formation process is proposed on the basis of mechanistic studies.
引用
下载
收藏
页码：1863 / 1867
页数：5
相关论文
共 50 条
  • [1] Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Pyridazinones with Terminal Allenes
    Parveen, Shaista
    Li, Changkun
    Hassan, Abbas
    Breit, Bernhard
    ORGANIC LETTERS, 2017, 19 (09) : 2326 - 2329
  • [2] Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Triazoles with Internal Alkynes and Terminal Allenes
    Berthold, Dino
    Breit, Bernhard
    ORGANIC LETTERS, 2018, 20 (03) : 598 - 601
  • [3] Rhodium-Catalyzed Chemo-, Regio-, and Enantioselective Allylation of 2-Aminothiazoles with Terminal Allenes
    Zheng, Jun
    Woerl, Benjamin
    Breit, Bernhard
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (31-32) : 5180 - 5182
  • [4] Rhodium-Catalyzed Chemodivergent Regio- and Enantioselective Allylic Alkylation of Indoles
    Sun, Minghe
    Liu, Min
    Li, Changkun
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (10) : 3457 - 3462
  • [5] Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation
    You, Cai
    Li, Xiuxiu
    Yang, Yuhong
    Yang, Yu-Sheng
    Tan, Xuefeng
    Li, Shuailong
    Wei, Biao
    Lv, Hui
    Chung, Lung-Wa
    Zhang, Xumu
    NATURE COMMUNICATIONS, 2018, 9
  • [6] Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation
    Cai You
    Xiuxiu Li
    Yuhong Yang
    Yu-Sheng Yang
    Xuefeng Tan
    Shuailong Li
    Biao Wei
    Hui Lv
    Lung-Wa Chung
    Xumu Zhang
    Nature Communications, 9
  • [7] Regio- and Enantioselective Synthesis of Chiral Pyrimidine Acyclic Nucleosides via Rhodium-Catalyzed Asymmetric Allylation of Pyrimidines
    Liang, Lei
    Xie, Ming-Sheng
    Qin, Tao
    Zhu, Man
    Qu, Gui-Rong
    Guo, Hai-Ming
    ORGANIC LETTERS, 2017, 19 (19) : 5212 - 5215
  • [8] Rhodium-Catalyzed Regio- and Enantioselective Allylic Sulfonylation from Sulfonyl Hydrazides
    Rehman, Sajid Ur
    Li, Changkun
    ORGANIC LETTERS, 2023, 25 (20) : 3693 - 3697
  • [9] Rhodium-catalyzed regio- and enantioselective amination of racemic secondary allylic trichloroacetimidates with N-methyl anilines
    Arnold, Jeffrey S.
    Cizio, Gregory T.
    Heitz, Drew R.
    Nguyen, Hien M.
    CHEMICAL COMMUNICATIONS, 2012, 48 (94) : 11531 - 11533
  • [10] Rhodium-catalyzed redox allylation reactions of ketones
    Williams, Florence J.
    Grote, Robin E.
    Jarvo, Elizabeth R.
    CHEMICAL COMMUNICATIONS, 2012, 48 (10) : 1496 - 1498
12345