56523-52-5Relevant academic research and scientific papers
ASYMMETRIC MICHAEL REACTION USING MACROCYCLIC LACTOSE DERIVATIVES AS CHIRAL CATALYSTS
Alonso-Lopez, Manuel,Martin-Lomas, Manuel,Penades, Soledad
, p. 3551 - 3554 (1986)
Macrocyclic lactose derivates complexed to potassium bases catalysed the Michael addition of phenyl- and naphthylacetic esters to methyl acrylate to give the corresponding adducts in enantiomeric excess ranging from 20 to 7o percent.
Chiral Lithium 2-Aminoalkoxides as Reagents for Enantioselective Michael Reaction
Kumamoto, Takuya,Aoki, Shin,Nakajima, Makoto,Koga, Kenji
, p. 1431 - 1432 (1994)
Chiral lithium alkoxides were designed and applied to enantioselective Michael reaction of methyl phenylacetate and methyl acrylate to give the corresponding adduct in enantiomeric excess up to 84percent.The catalytic enantioselective Michael reaction is
Enantioselective Michael addition catalyzed by chiral tripodal oxazoline-tBuOK complexes
Kim, Sung-Gon,Han Ahn, Kyo
, p. 4175 - 4177 (2001)
Benzene-based tripodal oxazolines are found to be novel chiral ligands for the catalytic enantioselective Michael addition via potassium enolates. Thus, methyl phenylacetate undergoes 1,4-addition to methyl acrylate using a catalytic amount of a tBuOK-oxa
New chiral crown ethers derived from camphor and their application to asymmetric Michael addition. First attempts to rationalize enantioselection by AM1 and AMBER calculations
Brunet,Poveda,Rabasco,Oreja,Font,Batra,Rodriguez- Ubis
, p. 935 - 948 (1994)
The synthesis of novel optically active crown ethers derived from (1R)- (+)-camphor is described. The mechanism of their catalytic effect upon the Michael addition of phenylacetate to acrylate is discussed in terms of kinetic vs. thermodynamic control in
Asymmetric Michael reaction. Deracemization of enolate by chiral crown ether
Toke, Laszlo,Fenichel, Laszlo,Albert, Melinda
, p. 5951 - 5954 (1995)
Crown ethers anellated to sugar units have been used to catalyse the enantioselective carbon-carbon bond forming reaction of methyl phenylacetate with methyl acrylate. A novel CH-acid deracemization has also been discovered in this study.
Stereocontrol in radical cyclization: Change in rate-determining step
Hakim, Siddiki S. M. A.,Sugimura, Takashi
supporting information; experimental part, p. 3626 - 3629 (2010/10/04)
Intramolecular cyclization of an α-carbon radical of ester carrying a chiral 2,4-pentanediol tether shows low stereoselectivity when the radical carbon has an alkyl substituent, while the selectivity becomes high to give a single stereoisomer (>99% pure)
Transformation of linear oligoketosides into macrocyclic neoglycoconjugates
Dondoni, Alessandro,Marra, Alberto
scheme or table, p. 3593 - 3596 (2009/09/28)
The macrocyclization of linear d-galacto-2-heptulopyranose-containing oligoketosides has been carried out by intramolecular glycosidation and ring-closing metathesis. The aglycon fragment of the cyclic neglycoconjugates thus formed was an alkylidene or a
Asymmetric Michael addition and deracemization of enolate by chiral crown ether
Toke, Laszlo,Bako, Peter,Keseru, Gyoergy M.,Albert, Melinda,Fenichel, Laszlo
, p. 213 - 222 (2007/10/03)
Crown ethers anellated to glucose units have been used to catalyse the enantioselective Michael addition of methyl phenylacetate to methyl acrylate in high chemical yields in up to 84% enantiomeric excess. A novel CH-acid deracemization has also been disc
Applications of Phase-Transfer Catalysis, 55. - New Experiments towards Enantioselective Phase-Transfer Catalysis with Optically Active Crown Ethers
Dehmlow, Eckehard V.,Knufinke, Volker
, p. 283 - 286 (2007/10/02)
Optically active crown ethers 1a - 1o, 2, 3a, b, 4a, b, 5a - 5d, 6a, b and the acyclic analogue 7 were used for three Michael-type additions, benzoin condensation, a C-alkylation, a base-catalyzed autoxidation and a hypochlorite epoxidation.Important obse
NEW SYNTHETIC STRATEGY TO HIGHLY SYMMETRIC CHIRAL MACROCYCLES FROM CARBOHYDRATE DERIVATIVES
Vicent, Cristina,Martin-Lomas, Manuel,Penades, Soledad
, p. 3605 - 3612 (2007/10/02)
A simple strategy for the synthesis of highly symmetric macrocycles incorporating carbohydrates is presented.The application of this strategy to the synthesis of optically active tetra-gluco-24-crown-8 (1), bis-gluco-15-crown-5 (3), and bis-gluco-21-crown
