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

被引:22
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 44 条
[1]   Applications of asymmetric organocatalysis in medicinal chemistry [J].
Aleman, Jose ;
Cabrera, Silvia .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) :774-793
[2]   Enantioselective Construction of Tetrasubstituted Stereogenic Carbons through Bronsted Base Catalyzed Michael Reactions: α′-Hydroxy Enones as Key Enoate Equivalent [J].
Badiola, Eider ;
Fiser, Bela ;
Gomez-Bengoa, Enrique ;
Mielgo, Antonia ;
Olaizola, Iurre ;
Urruzuno, Inaki ;
Garcia, Jesus M. ;
Odriozola, Jose M. ;
Razkin, Jesus ;
Oiarbide, Mikel ;
Palomo, Claudio .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (51) :17869-17881
[3]   Metal-Free Asymmetric 1,3-Dipolar Cycloaddition of N-Arylmaleimides to Azomethine Ylides Catalyzed by Chiral Tertiary Amine Thiourea [J].
Bai, Jian-Fei ;
Wang, Liang-Liang ;
Peng, Lin ;
Guo, Yun-Long ;
Ming, Jun-Nan ;
Wang, Fei-Ying ;
Xu, Xiao-Ying ;
Wang, Li-Xin .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (23) :4472-4478
[4]   Enantioselective Bronsted Base Catalysis with Chiral Cyclopropenimines [J].
Bandar, Jeffrey S. ;
Lambert, Tristan H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) :5552-5555
[5]   Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine [J].
Bui, Tommy ;
Syed, Salahuddin ;
Barbas, Carlos F., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8758-+
[6]  
Choubane H, 2018, CHEM COMMUN, V54, P3399, DOI [10.1039/C8CC01479E, 10.1039/c8cc01479e]
[7]   Multi-component syntheses of heterocycles by transition-metal catalysis [J].
D'Souza, Daniel M. ;
Mueller, Thomas J. J. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1095-1108
[8]   N-Heterocyclic Carbene-Catalyzed Umpolung of Imines for the Enantioselective Synthesis of Dihydroquinoxalines [J].
Das, Tamal Kanti ;
Ghosh, Avik ;
Balanna, Kuruva ;
Behera, Pradipta ;
Gonnade, Rajesh G. ;
Marelli, Udaya Kiran ;
Das, Abhijit Kumar ;
Biju, Akkattu T. .
ACS CATALYSIS, 2019, 9 (05) :4065-4071
[9]   Intramolecular hydrogen-bonding-assisted phosphine-catalysed [3+2] cyclisation of ynones with o-hydroxy/amino benzaldehydes [J].
Deng, Zhi-Xiong ;
Xie, Zhen-Zhen ;
Zheng, Yu ;
Xiao, Jun-An ;
Wang, Rui-Jia ;
Xiang, Hao-Yue ;
Yang, Hua .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (08) :2187-2191
[10]   Organocatalytic, Enantioselective Synthesis of VNI: A Robust Therapeutic Development Platform for Chagas, a Neglected Tropical Disease [J].
Dobish, Mark C. ;
Villalta, Fernando ;
Waterman, Michael R. ;
Lepesheva, Galina I. ;
Johnston, Jeffrey N. .
ORGANIC LETTERS, 2012, 14 (24) :6322-6325