New bifunctional 1,3-diamine organocatalysts derived from (+)-camphoric acid for asymmetric Michael addition of 1,3-dicarbonyl compounds to nitroolefins.
Sign Up to like & getrecommendations! Published in 2022 at "Chirality"
DOI: 10.1002/chir.23424
Abstract: Novel 1,3-diamine-derived bifunctional thiourea and squaramide organocatalysts were synthesized from (+)-camphoric acid. These catalysts were easily obtained in up to two to five synthetic steps, in a flexible approach that facilitates their structure variation. Their… read more here.
Keywords: addition dicarbonyl; asymmetric michael; michael addition; camphoric acid ... See more keywords
Chitosan-supported cinchona urea: Sustainable organocatalyst for asymmetric Michael reaction
Sign Up to like & getrecommendations! Published in 2020 at "Catalysis Communications"
DOI: 10.1016/j.catcom.2020.106132
Abstract: Abstract A novel chitosan-supported cinchona urea heterogeneous catalyst was developed for asymmetric reaction. The catalytic activity of the chitosan-supported organocatalyst was examined in the asymmetric Michael addition reaction to give chiral adducts in good yields… read more here.
Keywords: cinchona urea; supported cinchona; asymmetric michael; chitosan supported ... See more keywords
Organophosphine bearing multiple hydrogen-bond donors for asymmetric Michael addition reaction of 1-oxoindane-2-carboxylic acid ester via dual-reagent catalysis
Sign Up to like & getrecommendations! Published in 2020 at "Chinese Chemical Letters"
DOI: 10.1016/j.cclet.2020.07.026
Abstract: Abstract Multiple hydrogen bonds containing nucleophilic phosphines derived from dipeptide dual-reagents catalyzed asymmetric Michael addition reactions between indene esters and activated olefins in high yields and good to excellent enantioselectivities under mild reaction conditions. The… read more here.
Keywords: asymmetric michael; michael addition; reaction; multiple hydrogen ... See more keywords
Asymmetric Michael addition reaction organocatalyzed by stereoisomeric pyrrolidine sulfinamides under neat conditions. A brief study of self-disproportionation of enantiomers
Sign Up to like & getrecommendations! Published in 2017 at "Tetrahedron"
DOI: 10.1016/j.tet.2017.05.016
Abstract: Abstract This paper describes the synthesis of all four possible stereoisomers of the pyrrolidine sulfinamides derived from (S)-proline or (R)-proline and either enantiomer of t-butylsulfinamide. These bifunctional derivatives were examined as organocatalysts in the asymmetric… read more here.
Keywords: michael addition; asymmetric michael; reaction; pyrrolidine sulfinamides ... See more keywords
Chiral Functionalization of a Zirconium Metal-Organic Framework (DUT-67) as a Heterogeneous Catalyst in Asymmetric Michael Addition Reaction.
Sign Up to like & getrecommendations! Published in 2018 at "Inorganic chemistry"
DOI: 10.1021/acs.inorgchem.7b02854
Abstract: DUT-67, an 8-connected zirconium and 2,5-thiophenedicarboxylate-based metal-organic framework (MOF), was postsynthetically functionalized by l-proline via solvent-assisted linker incorporation to obtain a chiral base catalyst. The parent monocarboxylate could be almost completely exchanged by l-proline after… read more here.
Keywords: catalyst asymmetric; metal organic; asymmetric michael; catalyst ... See more keywords
Biocatalytic Asymmetric Michael Additions of Nitromethane to α,β-Unsaturated Aldehydes via Enzyme-bound Iminium Ion Intermediates
Sign Up to like & getrecommendations! Published in 2019 at "ACS Catalysis"
DOI: 10.1021/acscatal.9b00780
Abstract: The enzyme 4-oxalocrotonate tautomerase (4-OT) exploits an N-terminal proline as main catalytic residue to facilitate several promiscuous C–C bond-forming reactions via enzyme-bound enamine intermediates. Here we show that the active site of this enzyme can… read more here.
Keywords: unsaturated aldehydes; enzyme bound; enzyme; asymmetric michael ... See more keywords
Catalytic, Asymmetric Michael-Aldol Annulations via a Stereodivergent/Stereoconvergent Path Operating under Curtin-Hammett Control.
Sign Up to like & getrecommendations! Published in 2023 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.3c03373
Abstract: A bifunctional iminophosphorane (BIMP)-catalyzed method for the synthesis of densely functionalized cyclohexanols establishes five contiguous stereocenters (diastereoselection up to >20:1, enantioselectivity up to >99:1) in a Michael/aldol domino reaction between trisubstituted electrophilic alkenes and γ-nitroketones.… read more here.
Keywords: asymmetric michael; michael aldol; curtin hammett; michael ... See more keywords
A novel chiral surfactant-type metallomicellar catalyst for asymmetric Michael addition in water.
Sign Up to like & getrecommendations! Published in 2020 at "Chemical communications"
DOI: 10.1039/d0cc04410e
Abstract: A series of Schiff-based ligands consisting of both tertiary amines and lipophilic groups were designed and synthesized. Using these ligands, a new chiral surfactant-type metallomicellar catalyst was developed in water, and this was identified by… read more here.
Keywords: surfactant type; water; type metallomicellar; asymmetric michael ... See more keywords
Experimental and computational studies on the Cinchona anchored calixarene catalysed asymmetric Michael addition reaction.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d2cc02422e
Abstract: Lower-rim Cinchona anchored calix[4]arene cationic catalysts were developed for asymmetric Michael addition of acetylacetone to β-nitrostyrenes. The desired Michael adducts were formed with high yields and enantioselectivities. Density functional theory investigations throw light on the… read more here.
Keywords: reaction; cinchona anchored; asymmetric michael; michael addition ... See more keywords
Organocatalytic Asymmetric Michael Addition of Ketones to α, β-Unsaturated Nitro Compounds
Sign Up to like & getrecommendations! Published in 2020 at "Catalysts"
DOI: 10.3390/catal10060618
Abstract: An organic catalyst “(R, R)-1,2-diphenylethylenediamine(DPEN) derivative’’ was devel-oped as a chiral bifunctional organocatalyst and applied for asymmetric Michael additions of aromatic ketones to trans-β-nitroalkene compounds under neutral conditions. The isopropyl-subs-tituted thiourea catalyst in neutral condition… read more here.
Keywords: ketones unsaturated; michael; organocatalytic asymmetric; michael addition ... See more keywords
Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives
Sign Up to like & getrecommendations! Published in 2022 at "Molecules"
DOI: 10.3390/molecules27123797
Abstract: γ-Aminobutyric acid (GABA) represents one of the most prolific structural units widely used in the design of modern pharmaceuticals. For example, β-substituted GABA derivatives are found in numerous neurological drugs, such as baclofen, phenibut, tolibut,… read more here.
Keywords: asymmetric michael; substituted gaba; michael addition; addition synthesis ... See more keywords