Recent advances in intramolecular kinetic resolution reactions

被引:11
作者
Peng, Tianyu [1 ]
Li, Shixin [1 ]
Yang, Dongxu [1 ]
Wang, Linqing [1 ]
机构
[1] Lanzhou Univ, Sch Basic Med Sci, Res Unit Peptide Sci 2019RU066, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 13期
关键词
PROPARGYL CLAISEN REARRANGEMENT; RING-CLOSING METATHESIS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; HYDROXY ESTERS; ALCOHOLS; COMPLEXES; KETONES; DESYMMETRIZATION; DEAROMATIZATION;
D O I
10.1039/d3qo00563a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Kinetic resolution is a practical method that affords recovered starting materials and products in high enantiomeric excess from relatively simple racemic starting materials. However, intramolecular kinetic resolution is less reported due to its high reliance on designed substrates and catalysts that must match perfectly compared to intermolecular pathways. In this review, achievements in intramolecular kinetic resolution have been summarized and systematically discussed. The current review is divided into five sections based on different reaction types, mainly including cyclization, elimination, isomerization, rearrangement and miscellaneous reactions. The aim of this review article is to highlight the importance and elegance of this specialized resolution pathway in the construction of important and attractive chiral skeletons.
引用
收藏
页码:3401 / 3428
页数:28
相关论文
共 101 条
  • [1] Reductive Amination in the Synthesis of Pharmaceuticals
    Afanasyev, Oleg, I
    Kuchuk, Ekaterina
    Usanov, Dmitry L.
    Chusov, Denis
    [J]. CHEMICAL REVIEWS, 2019, 119 (23) : 11857 - 11911
  • [2] Enantioselective Robinson-Type Annulation Reaction Catalyzed by Chiral Phosphoric Acids
    Akiyama, Takahiko
    Katoh, Takuya
    Mori, Keiji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) : 4226 - 4228
  • [3] The Rauhut-Currier reaction: a history and its synthetic application
    Aroyan, Carrie E.
    Dermenci, Alpay
    Miller, Scott J.
    [J]. TETRAHEDRON, 2009, 65 (21) : 4069 - 4084
  • [4] Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes
    Bohan, Patrick T.
    Toste, F. Dean
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (32) : 11016 - 11019
  • [5] Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates
    Butt, Nicholas A.
    Zhang, Wanbin
    [J]. CHEMICAL SOCIETY REVIEWS, 2015, 44 (22) : 7929 - 7967
  • [6] Claisen rearrangement over the past nine decades
    Castro, AMM
    [J]. CHEMICAL REVIEWS, 2004, 104 (06) : 2939 - 3002
  • [7] Organocatalytic kinetic resolution via intramolecular aldol reactions: Enantioselective synthesis of both enantiomers of chiral cyclohexenones
    Chen, Liujuan
    Luo, Sanzhong
    Li, Jiuyuan
    Li, Xin
    Cheng, Jin-Pei
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (11) : 2627 - 2632
  • [8] Bronsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo- and Enantioselective Synthesis of Spirolactams
    Chen, Peng-Fei
    Zhou, Bo
    Wu, Peng
    Wang, Binju
    Ye, Long-Wu
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (52) : 27164 - 27170
  • [9] Recent Progress in (Dynamic) Kinetic Resolution Catalyzed by N-Heterocyclic Carbenes
    Chen, Shihao
    Shi, Yu-Hua
    Wang, Ming
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2184 - 2194
  • [10] Recent Advances in Kinetic Resolution of Tertiary Alcohols
    Chen Yunrong
    Liu Wei
    Yang Xiaoyu
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (03) : 679 - 697