Intramolecular Hydrogen-Bond Activation: Strategies, Benefits, and Influence in Catalysis

被引：19
|
作者：
Guerrero-Corella, Andrea [1 ]
Fraile, Alberto [1 ,2 ]
Aleman, Jose [1 ,2 ]
机构：
[1] Univ Autonoma Madrid, Dept Organ Chem, Modulo 1, Madrid 28049, Spain
[2] Univ Autonoma Madrid, Inst Adv Res Chem Sci IAdChem, Madrid 28049, Spain
来源：
ACS ORGANIC & INORGANIC AU | 2022年 / 2卷 / 03期
基金：
欧洲研究理事会;
关键词：
intramolecular activation; hydrogen bonding; organocatalysis; metal catalysis; bifunctional catalysis; asymmetric synthesis; ENANTIOSELECTIVE TRANSFER HYDROGENATION; AZOMETHINE YLIDES; MICHAEL ADDITION; CYCLOADDITION; IMINES; DONORS;
D O I：
10.1021/acsorginorgau.1c00053
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The activation of molecules through intramolecular hydrogen-bond formation to promote chemical reactions appears as a suitable strategy in organic synthesis, especially for the preparation of chiral compounds under metal and organocatalytic conditions. The use of this interaction has enabled reactivity enhancement of reagents, as well as stabilization of the chemical species and enantiocontrol of the processes.
引用
收藏
页码：197 / 204
页数：8
相关论文
共 50 条
  • [21] Dual Hydrogen-Bond/Enamine Catalysis Enables a Direct Enantioselective Three-Component Domino Reaction
    Rahaman, Hasibur
    Madarasz, Adam
    Papai, Imre
    Pihko, Petri M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) : 6123 - 6127
  • [22] The first organocatalytic addition of 2-trimethylsilyloxyfuran to carbonyl compounds:: hydrogen-bond catalysis in γ-butenolides synthesis
    De Rosa, Margherita
    Citro, Lucia
    Soriente, Annunziata
    TETRAHEDRON LETTERS, 2006, 47 (48) : 8507 - 8510
  • [23] Asymmetric Organocatalytic Michael/Henry Domino Reactions through Hydrogen-Bond Activation: Kinetic Access to Indane Scaffolds Bearing cis-Vicinal Substituents
    Loh, Charles C. J.
    Atodiresei, Iuliana
    Enders, Dieter
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (33) : 10822 - 10826
  • [24] KALIBORITE - AN EXAMPLE OF A CRYSTALLOGRAPHICALLY SYMMETRICAL HYDROGEN-BOND
    BURNS, PC
    HAWTHORNE, FC
    CANADIAN MINERALOGIST, 1994, 32 : 885 - 894
  • [25] Enantiocontrol with a Hydrogen-bond Directing Pyrrolidinylsilanol Catalyst
    Min, Taewoo
    Fettinger, James C.
    Franz, Annaliese K.
    ACS CATALYSIS, 2012, 2 (08): : 1661 - 1666
  • [26] Three is company: dual intramolecular hydrogen-bond enabled carboxylic acid active in ring-opening polymerization
    Xu, Jiaxi
    Liu, Jingjing
    Li, Zhenjiang
    Li, Xiaopei
    Chen, Cheng
    Zhao, Chengxu
    Xu, Songquan
    Pan, Xianfu
    Liu, Jiaqi
    Guo, Kai
    POLYMER CHEMISTRY, 2016, 7 (05) : 1111 - 1120
  • [27] Organocatalytic enantioselective and (Z)-selective allylation of 3-indolylmethanol via hydrogen-bond activation
    Liu, Yan
    Zhang, Hong-Hao
    Zhang, Yu-Chen
    Jiang, Yan
    Shi, Feng
    Tu, Shu-Jiang
    CHEMICAL COMMUNICATIONS, 2014, 50 (81) : 12054 - 12057
  • [28] An Atropo-enantioselective Synthesis of Benzo-Linked Axially Chiral Indoles via Hydrogen-Bond Catalysis
    Liu, Jin-Yu
    Yang, Xie-Chao
    Liu, Zhen
    Luo, Yong-Chun
    Lu, Hong
    Gu, Yu-Cheng
    Fang, Ran
    Xu, Peng-Fei
    ORGANIC LETTERS, 2019, 21 (13) : 5219 - 5224
  • [29] New architectures in hydrogen bond catalysis
    Rodriguez, Andrew A.
    Yoo, Hoseong
    Ziller, Joseph W.
    Shea, Kenneth J.
    TETRAHEDRON LETTERS, 2009, 50 (49) : 6830 - 6833
  • [30] Development of Tartaric Acid Derived Hydrogen-Bond Donors
    Lauber, Markus Boris
    Froehlich, Roland
    Paradies, Jan
    SYNTHESIS-STUTTGART, 2012, 44 (20): : 3209 - 3215
12345