ChemInform Abstract: Asymmetric Michael Reaction of Arylacetyl Phosphonates to Nitroalkenes with Bifunctional Amine-Thiourea Catalyst Bearing Multiple-Hydrogen-Bond Donor: Efficient Construction of Chiral α-Substituted Carboxylic Ester Compounds.

ChemInform ◽  
2016 ◽  
Vol 47 (38) ◽  
Author(s):  
Ming-Liang Zhang ◽  
Lin Chen ◽  
Yong You ◽  
Zhen-Hua Wang ◽  
Deng-Feng Yue ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Michael Reaction ◽  
Hydrogen Bond Donor ◽  
Carboxylic Ester ◽  
Multiple Hydrogen Bond ◽  
Efficient Construction ◽  
Asymmetric Michael Reaction

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>

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