Photochemical Synthesis of Chiral Heterocycles via Asymmetric Carbon-Heteroatom Bond Formation

被引:5
作者
Sharma, Yogesh Brijwashi [1 ]
Saha, Sanjukta [1 ]
Guru, Murali Mohan [1 ]
机构
[1] Natl Inst Pharmaceut Educ & Res, Dept Med Chem, Kolkata 700054, India
关键词
Asymmetric synthesis; carbon-heteroatom bond; visible light; photocatalysis; chiral heterocycle; photosensitizer; RADICAL-CROSSOVER CYCLOADDITIONS; ANTI-MARKOVNIKOV HYDROAMINATION; VISIBLE-LIGHT PHOTOCATALYSIS; UNACTIVATED ALKENES; ENANTIOSELECTIVE SYNTHESIS; PHOTOREDOX CATALYSIS; CYCLIZATION; ACTIVATION; AMIDE; METHYLENOLACTOCIN;
D O I
10.1002/adsc.202400307
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Chiral heterocyclic compounds play a crucial role in the pharmaceutical science, materials science, and agrochemical industries. The critical step for synthesizing chiral heterocycles is the formation of asymmetric carbon-heteroatom bonds, which can be achieved in a chiral environment under thermal or photochemical conditions. However, photochemical asymmetric transformation has become an area of immense growth in the past 15 years. In the drug discovery and development era, chiral photochemical transformations have drawn the attention of researchers to develop new synthetic strategies for chiral heterocycles via asymmetric carbon-heteroatom bond formation. Chiral photochemistry in the pathway of asymmetric synthesis requires a chirality source which is transferred to the products. A catalytic chiral metal complexing agent or a chiral photosensitizer that generally follows a single electron transfer (SET) or oxidative and reductive quenching cycle has been widely exploited to achieve this goal. In this review, we have demonstrated the recent development of photochemical synthesis of chiral heterocycles via asymmetric carbon-heteroatom bond formation by using a chiral metal catalyst, asymmetric organocatalyst, or dual catalytic system based on their plausible mechanism. image
引用
收藏
页码:2432 / 2449
页数:18
相关论文
共 50 条
  • [31] Recent advances in the synthetic and mechanistic aspects of the ruthenium-catalyzed carbon-heteroatom bond forming reactions of alkenes and alkynes
    Yi, Chae S.
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) : 76 - 80
  • [32] The hetero-Friedel-Crafts-Bradsher Cyclizations with Formation of Ring Carbon-Heteroatom (P, S) Bonds, Leading to Organic Functional Materials
    Skalik, Joanna
    Koprowski, Marek
    Rozycka-Sokolowska, Ewa
    Balczewski, Piotr
    [J]. MATERIALS, 2020, 13 (21) : 1 - 25
  • [33] Recent Advances in Light-Driven Carbon-Carbon Bond Formation via Carbon Dioxide Activation
    Jung, Jieun
    Saito, Susumu
    [J]. SYNTHESIS-STUTTGART, 2021, 53 (18): : 3263 - 3278
  • [34] Asymmetric Methods for Carbon-Fluorine Bond Formation
    Remete, Attila M.
    Nonn, Melinda
    Escorihuela, Jorge
    Fustero, Santos
    Kiss, Lorand
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (44) : 5946 - 5974
  • [35] Asymmetric synthesis of α,γ-substituted γ-sultones via allylation of chiral lithiated Sulfonates
    Enders, D
    Harnying, W
    Vignola, N
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (20) : 3939 - 3947
  • [36] Asymmetric Synthesis of Remotely Chiral Naphthols and Naphthylamines via Naphthoquinone Methides
    Liu, Shuxuan
    Chan, Ka Lok
    Lin, Zhenyang
    Sun, Jianwei
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (23) : 12802 - 12811
  • [37] Chiral Phase-Transfer Catalysts with Hydrogen Bond: A Powerful Tool in the Asymmetric Synthesis
    Wang, Hongyu
    [J]. CATALYSTS, 2019, 9 (03):
  • [38] Chiral Aryliodine-Catalyzed Asymmetric Oxidative C-N Bond Formation via Desymmetrization Strategy
    Ding, Qiang
    He, Huan
    Cai, Qian
    [J]. ORGANIC LETTERS, 2018, 20 (15) : 4554 - 4557
  • [39] Highly Stereoselective Synthesis of Fluoroalkene Dipeptides via the Novel Chromium(II)-Mediated Carbon-Fluorine Bond Cleavage/New Carbon-Carbon Bond Formation
    Nihei, Takashi
    Nishi, Yuji
    Ikeda, Natsumi
    Yokotani, Saya
    Ishihara, Takashi
    Arimitsu, Satoru
    Konno, Tsutomu
    [J]. SYNTHESIS-STUTTGART, 2016, 48 (06): : 865 - 881
  • [40] Synthesis of Chiral Amines via Asymmetric Hydrogen Borrowing
    Wang, Kun
    Xiao, Miao
    Wang, Chao
    [J]. SYNLETT, 2021, 32 (08) : 743 - 751