Search results for "enantioselective synthesis"
showing 10 items of 418 documents
Asymmetric synthesis of (−)-pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions
2001
Abstract A ring-opening reaction of N -methylaziridines with Boc 2 O/NaI has been applied to the asymmetric synthesis of pseudoephedrine. 3-Methylamino-3-phenyl-1,2-propanediol 1 , derived from (2 S ,3 S )-3-phenyloxiran-2-ylmethanol, was converted into the oxazolidin-2-one 4 , a precursor of pseudoephedrine. The reaction occurs with a stereospecific interchange of amino and alcohol functions.
Organocatalytic Enantioselective Synthesis of α-Hydroxyketones through a Friedel−Crafts Reaction of Naphthols and Activated Phenols with Aryl- and Al…
2016
[EN] An efficient organocatalytic asymmetric synthesis of alpha-hydroxyketones has been developed. Quinine-derived thiourea catalyzed the enantioselective Friedel Crafts alkylation of naphthols and activated phenols with aryl- and alkylglyoxal hydrates, providing the corresponding chiral alpha-hydroxyketones with high yields (up to 97%) and excellent enantioselectivities (up to 99% ee).
Organocatalytic Enantioselective Synthesis of Pyrazoles Bearing a Quaternary Stereocenter
2016
An efficient one-pot asymmetric synthesis of pyrazoles bearing a chiral quaternary stereocenter has been developed. Quinine-derived thiourea catalyzed the enantioselective addition of pyrazolones to isatin-derived ketimines, providing the corresponding acetylated pyrazoles after in situ treatment with Ac2O/Et3N. The corresponding pyrazoles were afforded in high yields and excellent enantioselectivities.
Enantioselective addition of nitromethane to α-keto esters catalyzed by copper(ii)–iminopyridine complexes
2008
The copper complex of a chiral iminopyridine easily prepared from (R)-(-)-fenchone and picolylamine catalyzes the enantioselective Henry (nitroaldol) reaction between nitromethane and alpha-keto esters. Good yields and modest to good enantioselectivities are obtained for a wide range of alpha-keto esters, bearing aromatic, alkyl or alkenyl groups attached to the ketone carbonyl group.
Kinetic Modeling of Ethyl Benzoylformate Enantioselective Hydrogenation over Pt/Al2O3
2014
A kinetic model was developed for the enantioselective hydrogenation of ethyl benzoylformate (EBF) on a modified Pt/Al2O3 catalyst. This model was based on the assumption of different numbers of si...
Enantioselective Henry addition of methyl 4-nitrobutyrate to aldehydes. Chiral building blocks for 2-pyrrolidinones and other derivatives.
2010
A catalytic highly enantioselective Henry addition of methyl 4-nitrobutyrate to aldehydes using a Cu(II)-amino pyridine complex as catalyst is described. The products resulting from this reaction constitute a new, highly versatile family of chiral building blocks as a result of the presence of three different functional groups on the molecule. These products have been transformed into nonracemic chiral gamma-lactams, 5-hydroxy-5-substituted levulinic acid derivatives, and delta-lactones.
Combining organocatalysis and lanthanide catalysis: a sequential one-pot quadruple reaction sequence/hetero-Diels-Alder asymmetric synthesis of funct…
2016
A stereoselective one-pot synthesis of functionalized complex tricyclic polyethers has been achieved using the combination of secondary amine and lanthanide catalysis. This one-pot quadruple reaction/Hetero-Diels–Alder sequence gave good yields (per step) as well as excellent diastereo- and enantioselectivities. Furthermore, the particular combination of lanthanide complexes with organocatalysis is one of the first examples described for sequential catalysis.
Catalytic Diastereo- and enantioselective vinylogous Mannich reaction of alkylidenepyrazolones to isatin-derived ketimines
2021
A valuable organocatalytic vinylogous Mannich reaction between alkylidenepyrazolones and isatin-derived ketimines has been successfully established. Squaramide organocatalyst, prepared from quinine, catalyzed the diastereo- and enantioselective vinylogous Mannich addition, affording a range of aminooxindole-pyrazolone adducts (24 examples) with excellent outcomes: up to 98% yield with complete diastereoselectivity and excellent enantioselectivity (up to 99% ee). Additionally, different synthetic transformations were performed with the chiral pyrazolone-oxindole adducts.
Enantioselective α-alkylation of unsaturated carboxylic acids using a chiral lithium amide
2001
Abstract The regio- and stereochemistry of the alkylation of dienediolates from unsaturated carboxylic acids with benzylic halides, which often results in mixtures of isomers, can be controlled by means of changes in the lithium amide, allowing the α-regioisomer to be obtained as the major diastereoisomer. In addition, when chiral amines are used, moderate enantiomeric excesses can be attained.
ChemInform Abstract: Enantioselective α-Alkylation of Unsaturated Carboxylic Acids Using a Chiral Lithium Amide.
2010
Abstract The regio- and stereochemistry of the alkylation of dienediolates from unsaturated carboxylic acids with benzylic halides, which often results in mixtures of isomers, can be controlled by means of changes in the lithium amide, allowing the α-regioisomer to be obtained as the major diastereoisomer. In addition, when chiral amines are used, moderate enantiomeric excesses can be attained.