72709-62-7

Upstream product

• 102-96-5 (2-nitroethenyl)benzene 
• 141-97-9 ethyl acetoacetate 
• 5153-67-3 nitrostyrene 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 100-52-7 benzaldehyde 
• 75-52-5 nitromethane 
• 620-80-4 ethyl 2-benzylidene acetoacetate 

Downstream Products

• 82653-44-9 (2R,3R,2'S,3'S)-bis-(4-ethoxycarbonyl-2,3-dihydro-5-methyl-3-phenyl-2-furyl)hydroxylamine 
• 952393-72-5 1-(4-fluoro-phenyl)-2-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 81675-23-2 (2R,3R,2'S,3'S)-O-acetylbis-(4-ethoxycarbonyl-2,3-dihydro-5-methyl-3-phenyl-2-furyl)hydroxylamine 
• 3274-63-3 2-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Primary-secondary diamines catalyzed Michael reaction to generate chiral fluorinated quaternary carbon centers

Abstract Asymmetric Michael reactions of α-fluoro-β-ketoesters to nitroolefins have been achieved by using readily accessible primary-secondary diamines as the organocatalysts through enamine activation mode, affording the useful Michael adducts bearing c

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

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.

A nanoporous metal-organic framework as a renewable size-selective hydrogen-bonding catalyst in water

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

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

Tetraarylphosphonium inner-salts (TAPIS) as both Lewis base catalyst and phase tag

Tetraarylphosphonium inner-salts (TAPIS) have been designed, synthesized and verified as recyclable and reusable Lewis base catalysts. The resulted TAPIS catalyst has been successfully applied in Michael addition, cyanation and trifluoromethylation reactions.

Organocatalyzed asymmetric Michael addition by an efficient bifunctional carbohydrate-thiourea hybrid with mechanistic DFT analysis

A series of thiourea based bifunctional organocatalysts having d-glucose as a core scaffold were synthesized and examined as catalysts for the asymmetric Michael addition reaction of aryl/alkyl trans-β-nitrostyrenes over cyclohexanone and other Michael donors having active methylene. Excellent enantioselectivities (0. The obtained results were explained through DFT calculations using the B3LYP/6-311G(d,p)//B3LYP/6-31G(d) basic set. The QM/MM calculations revealed the role of cyclohexanone as a solvent as well as reactant in the rate determining step imparting 31.91 kcal mol?1 of energy towards the product formation.

Novel Chiral Bifunctional L-Thiazoline-Thiourea Derivatives: Design and Application in Enantioselective Michael Reactions

Several novel chiral bifunctional L-thiazoline-thiourea derivatives were easily synthesized from commercially available L-cysteine in high yield. These catalysts were subsequently applied to the enantioselective Michael addition of acetylacetone to β-nitr

Tris-ureas as versatile and highly efficient organocatalysts for Michael addition reactions of nitro-olefins: Mechanistic insight from in-situ diagnostics

Tris(2-aminoethyl)-amine, TREN based tris-ureas (1a–1d) and tris-thiourea (1e) have been explored towards a wide range of catalytic Michael addition reactions. These tris-ureas, 1a–1d efficiently catalyze the addition reaction of β-nitro styrenes (2a–2d)

Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters

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

Chiral squaramide-functionalized imidazolium-based organic-inorganic hybrid silica promotes asymmetric michael addition of 1,3-dicarbonyls to nitroalkenes in brine

Chiral cinchona-based squaramide-functionalized organic-inorganic hybrid silica is developed through postgrafting 3-mercaptopropyltrimethoxylsilane onto imidazolium-based organic-inorganic hybrid silica, followed by the anchor of a squaramide organocataly