Research Progress on Enantioselective Desymmetrization Reactions Involving Metal Carbenes

被引:11
|
作者
Teng Ming-Yu [1 ]
Han Tao [1 ]
Huang En-He [2 ]
Ye Long-Wu [1 ,2 ,3 ]
机构
[1] Yunan Normal Univ, Coll Chem & Chem Engn, Kunming 650500, Yunnan, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
diazo compounds; metal carbene; desymmetrization; aymmetric synthesis; C-H INSERTION; CARBON-HYDROGEN INSERTION; INTRAMOLECULAR BUCHNER REACTION; BOND INSERTION; ASYMMETRIC-SYNTHESIS; CATALYZED REACTIONS; ORGANIC-SYNTHESIS; DIAZOACETATES; DIAZOKETONES; ACTIVATION;
D O I
10.6023/cjoc202206041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Metal carbenes have been widely applied in organic synthesis, and they can undergo a variety of chemical transformations due to their versatile reactivities. In this review, the desymmetrization of C-H insertion reaction, Buchner reaction, Si-H insertion reaction and B-H insertion reaction involving metal carbenes is introduced according to the different reaction types of metal carbenes. Under the catalysis of chiral rhodium, ruthenium and copper catalysts, chiral carbocycles, heterocycles, organosilicons and organoborons can be obtained with high enantioselectivity, which greatly enriches the development of asymmetric synthetic chemistry.
引用
收藏
页码:3295 / 3301
页数:7
相关论文
共 74 条
  • [1] Brooks WH, 2011, CURR TOP MED CHEM, V11, P760
  • [2] Desymmetrization by Asymmetric Copper-Catalyzed Intramolecular C-H Insertion Reactions of α-Diazo-β-oxosulfones
    Brouder, Thomas A.
    Slattery, Catherine N.
    Ford, Alan
    Khandavilli, U. B. Rao
    Skorepova, Eliska
    Eccles, Kevin S.
    Lusi, Matteo
    Lawrence, Simon E.
    Maguire, Anita R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 7543 - 7563
  • [3] Buchner E., 1885, BER DTSCH CHEM GES, V18, P2377, DOI DOI 10.1002/CBER.188501802119
  • [4] Dirhodium Carboxylate Catalysts from 2-Fenchyloxy or 2-Menthyloxy Arylacetic Acids: Enantioselective C-H Insertion, Aromatic Addition and Oxonium Ylide Formation/Rearrangement
    Buckley, Aoife M.
    Crowley, Daniel C.
    Brouder, Thomas A.
    Ford, Alan
    Khandavilli, U. B. Rao
    Lawrence, Simon E.
    Maguire, Anita R.
    [J]. CHEMCATCHEM, 2021, 13 (20) : 4318 - 4324
  • [5] Transition-Metal-Catalyzed Intramolecular Nucleophilic Addition of Carbonyl Groups to Alkynes
    Chen, Lianfen
    Chen, Kai
    Zhu, Shifa
    [J]. CHEM, 2018, 4 (06): : 1208 - 1262
  • [6] Enantioselective copper catalysed C-H insertion reaction of 2-sulfonyl-2-diazoacetamides to form γ-lactams
    Clarke, Leslie Ann
    Ring, Aoife
    Ford, Alan
    Sinha, Abhijeet S.
    Lawrence, Simon E.
    Maguire, Anita R.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (38) : 7612 - 7628
  • [7] A REINVESTIGATION OF THE INTRAMOLECULAR BUCHNER REACTION OF 1-DIAZO-4-PHENYLBUTAN-2-ONES LEADING TO 2-TETRALONES
    CORDI, AA
    LACOSTE, JM
    HENNIG, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (01): : 3 - 4
  • [8] Copper-Mediated, Heterogeneous, Enantioselective Intramolecular Buchner Reactions of α-Diazoketones Using Continuous Flow Processing
    Crowley, Daniel C.
    Lynch, Denis
    Maguire, Anita R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07): : 3794 - 3805
  • [9] Catalytic asymmetric C-H activation of alkanes and tetrahydrofuran
    Davies, HML
    Hansen, T
    Churchill, MR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) : 3063 - 3070
  • [10] Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion
    Davies, HML
    Beckwith, REJ
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2861 - 2903