Enantioselective Construction of Spirooxindole Derivatives through [3+2] Annulation Catalyzed by a Bisthiourea as a Multiple-Hydrogen-Bond Donor

2012 ◽  
Vol 19 (6) ◽  
pp. 1914-1918 ◽  
Author(s):  
Yan Shi ◽  
Aijun Lin ◽  
Haibin Mao ◽  
Zhijie Mao ◽  
Weipeng Li ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bond Donor ◽  
Multiple Hydrogen Bond

Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis

2019 ◽  
Author(s):  
Mandeep K. Chahal ◽  
Daniel Payne ◽  
Yoshitaka Matsushita ◽  
Jan Labuta ◽  
Katsuhiko Ariga ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Molecular Engineering ◽  
Hydrogen Bond Donor ◽  
Conjugate Additions ◽  
Bond Forming ◽  
Michael Additions ◽  
New Class ◽  
Hydrogen Bonding Interactions ◽  
Multiple Hydrogen Bond ◽  
Intramolecular Hydrogen

<p>A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens with increased intramolecular hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond forming binding site. In this work we report the first example of non-planar OxPs as hydrogen-bond donor catalysts. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol%) under mild conditions. Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions.</p>

Selective host–guest interactions in metal–organic frameworks via multiple hydrogen bond donor–acceptor recognition sites

2019 ◽  
Vol 7 (17) ◽  
pp. 10379-10388 ◽  
Author(s):  
T. Wittmann ◽  
C. B. L. Tschense ◽  
L. Zappe ◽  
C. Koschnick ◽  
R. Siegel ◽  
...  
Keyword(s):  
Drug Delivery ◽  
Hydrogen Bond ◽  
Porous Materials ◽  
Metal Organic Frameworks ◽  
Hydrogen Bond Donor ◽  
Recognition Sites ◽  
Molecular Separation ◽  
Multiple Hydrogen Bond ◽  
Donor Acceptor ◽  
Metal Organic

Targeted recognition of medium sized molecules with mixed hydrogen bond units is essential for using porous materials for molecular separation, sensing and drug delivery.

Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis

2019 ◽  
Author(s):  
Mandeep K. Chahal ◽  
Daniel Payne ◽  
Yoshitaka Matsushita ◽  
Jan Labuta ◽  
Katsuhiko Ariga ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Molecular Engineering ◽  
Hydrogen Bond Donor ◽  
Conjugate Additions ◽  
Bond Forming ◽  
Michael Additions ◽  
New Class ◽  
Hydrogen Bonding Interactions ◽  
Multiple Hydrogen Bond ◽  
Intramolecular Hydrogen

<p>A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens with increased intramolecular hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond forming binding site. In this work we report the first example of non-planar OxPs as hydrogen-bond donor catalysts. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol%) under mild conditions. Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions.</p>

Aliphatic Carboxylic Acid as Hydrogen-Bond Donor for Converting CO2 and Epoxide into Cyclic Carbonate under Mild Conditions

2021 ◽  
Author(s):  
Zheng Wang ◽  
Yajun Wang ◽  
Qianjie Xie ◽  
Zhiying Fan ◽  
Yehua Shen
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Value Added ◽  
Cyclic Carbonate ◽  
Hydrogen Bond Donor ◽  
Title Reaction ◽  
Aliphatic Carboxylic Acid ◽  
Mild Conditions ◽  
Atmospheric Carbon

The coupling of CO2 and epoxide is promising way to reduce atmospheric carbon by converting it into value-added cyclic carbonate. Pursuing efficient catalysts is highly attractive for the title reaction....

Sign in / Sign up

Export Citation Format

Share Document