81675-18-5Relevant academic research and scientific papers
Investigation of lipase-catalyzed Michael-type carbon-carbon bond formations
Strohmeier, Gernot A.,Sovi?, Tanja,Steinkellner, Georg,Hartner, Franz S.,Andryushkova, Aleksandra,Purkarthofer, Thomas,Glieder, Anton,Gruber, Karl,Griengl, Herfried
, p. 5663 - 5668 (2009)
Conjugate additions of carbon nucleophiles to appropriate acceptor molecules were investigated with respect to the synthetic potential and stereochemistry of the products. Reactions of short-chain α,β-unsaturated ketones and mono-substituted nitroalkenes
Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis
Chahal, Mandeep K.,Payne, Daniel T.,Matsushita, Yoshitaka,Labuta, Jan,Ariga, Katsuhiko,Hill, Jonathan P.
supporting information, p. 82 - 90 (2020/01/02)
A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens having 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 describe the first example of non-planar OxPs as hydrogen-bond donor catalysts prepared using a molecular engineering approach of the binding site for dual activation of substrates. 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.
2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins
Togashi, Rei,Chennapuram, Madhu,Seki, Chigusa,Okuyama, Yuko,Kwon, Eunsang,Uwai, Koji,Tokiwa, Michio,Takeshita, Mitsuhiro,Nakano, Hiroto
, p. 3882 - 3889 (2019/06/21)
New optically active 2-azanorbornane-based amino alcohol organocatalysts were designed and synthesized, and these catalysts were successfully employed in the asymmetric Michael reaction of β-keto esters with nitroolefins to obtain the corresponding chiral
A nanoporous metal-organic framework as a renewable size-selective hydrogen-bonding catalyst in water
Liu, Yanhong,Ma, Ju,Wu, Pengyan,Zheng, Jia-Jia,Tian, Xueqin,Jiang, Min,He, Yumei,Dong, Han,Wang, Jian
, p. 11855 - 11861 (2019/08/14)
A novel squaramide-containing metal-organic framework (MOF) material has been designed and synthesized. A detailed X-ray crystal structure analysis showed that four squaramides of this MOF adopted two orientations in each dependent nanopore, confirming th
Squaramide-decorated covalent organic framework as a new platform for biomimetic hydrogen-bonding organocatalysis
Li, Xia,Wang, Zhifang,Sun, Jiaxing,Gao, Jia,Zhao, Yu,Cheng, Peng,Aguila, Briana,Ma, Shengqian,Chen, Yao,Zhang, Zhenjie
supporting information, p. 5423 - 5426 (2019/05/16)
A squaramide-decorated COF was synthesized and used as a highly efficient heterogeneous catalyst for hydrogen-bonding organocatalysis as exemplified in the context of catalyzing Michael addition reactions under mild conditions. Our work lays a foundation
Tertiary Amine-Derived Ionic Liquid-Supported Squaramide as a Recyclable Organocatalyst for Noncovalent "on Water" Catalysis
Tukhvatshin, Rinat S.,Kucherenko, Alexander S.,Nelyubina, Yulia V.,Zlotin, Sergei G.
, p. 2981 - 2989 (2017/05/31)
Chiral tertiary amine-derived ionic liquid-supported squaramide was synthesized from available precursors and applied as an efficient organocatalyst for asymmetric Michael additions of β-dicarbonyl compounds to α-nitroolefins in the presence of water. Cor
Bifunctional organocatalysis with squaramide-containing Dawson organo-polyoxotungstates
Lachkar, David,Lac?te, Emmanuel
, p. 113 - 116 (2016/03/22)
Two squaramide-containing organo-polyoxometalates (POMs) have been prepared, which efficiently catalyze the addition of dicarbonyl derivatives onto nitroolefins. The POM surface enhances the reactivity of the squaramide, and the hybrid acts as a bifunctio
CATALYST FOR ORGANIC REACTION AND METHOD OF USE THEREOF
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Paragraph 0094; 0118-0119, (2015/05/05)
A catalyst for an organic reaction and a method of using a catalyst in an organic reaction are provided. The catalyst for an addition or condensation reaction includes a graphene oxide including an oxygen functional group, and the catalyst is configured t
Modularly evolved 2-aminodmap/squaramides as highly active bifunctional organocatalysts in Michael addition
I?k, Murat,Unver, M. Yagiz,Tanyeli, Cihangir
, p. 828 - 835 (2015/03/03)
We report a new family of chiral bifunctional acid/base type organocatalysts, 2-aminoDMAP/Squaramides, which are proved to be highly active (1 mol % cat. loading) promoters in conjugate addition of dibenzoylmethane to various trans-β-nitroalkenes. Steric demand of the catalysts was clearly seen by a set-by-set modulation of the squaramide unit through electronic and steric factors. The synergistic cooperation of 2-aminoDMAP "uperbase" and sterically encumbered squaramide (H-bond donor) enabled complete conversion of a range of reactants into corresponding Michael adducts in a couple of hours with exquisite selectivities (up to 98% ee).
Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters
Chauhan, Pankaj,Mahajan, Suruchi,Raabe, Gerhard,Enders, Dieter
supporting information, p. 2270 - 2272 (2015/02/05)
An unprecedented stereoselective organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence between β-dicarbonyl compounds, β-nitroalkenes and 4-nitro-5-styrylisoxazoles sequentially catalyzed by low loading of a squaramide catalyst and an achiral base has b
