Search results for "Stereocenter"
showing 10 items of 123 documents
ChemInform Abstract: Enantioselective Addition of Nitromethane to 2-Acylpyridine N-Oxides. Expanding the Generation of Quaternary Stereocenters with …
2014
The direct asymmetric Henry reaction with prochiral ketones, leading to tertiary nitroaldols, is an elusive reaction so far limited to a reduced number of reactive substrates such as trifluoromethyl ketones or α-keto carbonyl compounds. Expanding the scope of this important reaction, the direct asymmetric addition of nitromethane to 2-acylpyridine N-oxides catalyzed by a BOX-Cu(II) complex to give the corresponding pyridine-derived tertiary nitroaldols having a quaternary stereogenic center with variable yields and good enantioselectivity, is described.
Catalytic Enantioselective Aza-Reformatsky Reaction with Cyclic Imines
2016
A catalytic highly enantioselective aza-Reformatsky reaction with cyclic aldimines and ketimines for the synthesis of chiral b-amino esters with good yields and excellent enantioselectivities is reported.Areadily available diaryl prolinol is used as a chiral ligand, ZnMe2 as a zinc source and ethyl iodoacetate as reagent in the presence of air atmosphere. The reaction with cyclic ketimines generates a quaternary stereocenter with excellent levels of enantioselectivity. Furthermore, five-membered N-sulfonyl ketimines were used as electrophiles with good enantiomeric excesses, under the optimized reaction conditions. Moreover, several chemical transformations were performed with the chiral b-…
Stereoselective synthesis of the naturally occurring 2-pyranone dodoneine
2008
The first total synthesis of the naturally occurring dihydropyranone dodoneine is reported. Asymmetric allylation reactions were used for the stereoselective generation of the two stereogenic centers. The pyranone ring was created by ring-closing metathesis. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
Enantiodifferentiation of acyclic phosphonium salts in chiral liquid crystalline solutions
2006
Abstract The enantiodifferentiation of acyclic phosphonium salts bearing a stereogenic centre, whether on the phosphorus atom or on one of its substituents, was investigated by 2 H–{ 1 H}, 13 C–{ 1 H} and 31 P–{ 1 H} NMR in chiral liquid crystals composed of a polypeptide dissolved in an organic solvent. For the first time, the enantiomers of P-chirogenic phosphorus compounds were discriminated in these anisotropic media, affording good to excellent separation of the signals, allowing the determination of their proportion. While 31 P–{ 1 H} NMR spectra showed no chiral separation, 2 H–{ 1 H} NMR was efficient in the enantiodifferentiation of an isotopically labelled compound. Better still, …
ChemInform Abstract: A Versatile Approach to CF3-Containing 2-Pyrrolidones by Tandem Michael Addition-Cyclization: Exemplification in the Synthesis o…
2016
The synthesis of new fluorinated pyrrolidones starting from unprotected amino esters and amino nitriles through a Michael addition-lactamization sequence is described. The resulting CF3 -containing building blocks, bearing a quaternary stereogenic center adjacent to the fluorinated group, have been converted into amino pyrrolidines that display potent β-secretase 1 (BACE1) inhibitory activity. This work constitutes an example of selective fluorination as a valid strategy for the modulation of physicochemical and biological properties of lead compounds in drug discovery.
Gold catalyzed stereoselective tandem hydroamination–formal aza-Diels–Alder reaction of propargylic amino esters
2013
A gold-catalyzed tandem intramolecular hydroamination-formal aza-Diels-Alder reaction of propargylic amino esters is described. The overall process leads to the formation of a tetracyclic framework as a single diastereoisomer, with the creation of four bonds and five stereocenters.
ChemInform Abstract: Gold-Catalyzed Tandem Hydroamination/Formal Aza-Diels-Alder Reaction of Homopropargyl Amino Esters: A Combined Computational and…
2015
Under optimized conditions, the title reaction leads to formation of a tetracyclic nitrogen-containing framework with generation of 4 bonds and 5 stereocenters.
Switchable Access to Different Spirocyclopentane Oxindoles by N-Heterocyclic Carbene Catalyzed Reactions of Isatin-Derived Enals and N-Sulfonyl Ketim…
2017
A novel NHC-catalyzed annulation protocol for the asymmetric synthesis of biologically important β-lactam fused spirocyclopentane oxindoles with four contiguous stereocenters, including two quaternary carbon centers, was developed. Alternatively, spirocyclopentane oxindoles containing an enaminone moiety can be achieved using the same starting materials, isatin-derived enals, and N-sulfonyl ketimines, in the presence of a slightly different NHC catalytic system. This switchable annulation strategy enables the selective assembly of both heterocyclic scaffolds with good yields and excellent enantioselectivities for a broad range of substrates.
Stereocontrolled synthesis of azeto[2,1-b] quinazolines bearing three stereocenters via the intramolecular [2+2] cycloaddition between ketenimines an…
2004
Abstract A highly stereoselective synthesis of azeto[2,1- b ]quinazolines bearing three stereocenters (C1, C2, and C8) has been achieved via intramolecular [2+2] cycloaddition between ketenimine and imine functions supported on an ortho -benzylic scaffold. An asymmetric center adjacent to the iminic nitrogen atom, the future C8 carbon of the bicyclic product, efficiently controls the absolute configuration of the two new stereogenic carbon atoms of the azetidine ring, C1 and C2.
ChemInform Abstract: Gold Catalyzed Stereoselective Tandem Hydroamination-Formal Aza-Diels-Alder Reaction of Propargylic Amino Esters.
2013
The overall sequence of the tandem reaction presented here leads to nitrogen-containing tetracycles under formation of 4 bonds and five stereocenters, in most cases as single diastereoisomers.