Category: 132098-59-0

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called High trans selectivity in the copper bis(oxazoline)-catalyzed asymmetric cyclopropanation of olefins by (trimethylsilyl)diazomethane, published in 2003-12-22, which mentions a compound: 132098-59-0, mainly applied to copper bisoxazoline asym cyclopropanation alkene trimethylsilyl diazomethane; stereoselective cyclopropanation copper bisoxazoline alkene trimethylsilyl diazomethane; olefin stereoselective cyclopropanation copper bisoxazoline trimethylsilyl diazomethane; cyclopropanecarboxylate phenyl preparation stereoselective cyclopropanation copper bisoxazoline trimethylsilyl diazomethane, Synthetic Route of C19H18N2O2.

Copper(I) bis(oxazoline) species are among the most enantioselective cyclopropanation catalysts that have been reported, although these catalysts generally give low diastereoselectivities. Greatly improved diastereoselectivities using (trimethylsilyl)diazomethane as the carbon source were observed Several bis(oxazoline) species that also give comparable or higher enantioselectivities with (trimethylsilyl)diazomethane compared to the more readily available Et diazoacetate were identified. The application of this methodol. to several olefins has been explored.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Computed Properties of C19H18N2O2. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane, is researched, Molecular C19H18N2O2, CAS is 132098-59-0, about Bis(oxazoline)titanium complexes as chiral catalysts for enantioselective hydrosilylation of ketones – a combined experimental and theoretical investigation. Author is Bandini, Marco; Bernardi, Fernando; Bottoni, Andrea; Cozzi, Pier Giorgio; Miscione, Gian Pietro; Umani-Ronchi, Achille.

A combined exptl. and theor. investigation has been carried out on a new catalytic system, based on bis(oxazoline) (BOX) complexes of titanium. These catalytic species are able to reduce aromatic ketones with good enantiomeric excesses and satisfactory yields. The exptl. and the computational (DFT) evidence has provided useful information on the nature of the active catalytic species and on the mechanism of the reaction. The most likely reaction path involves a TiIV catalytic species. This result agrees with exptl. obtained evidence that seems to rule out the presence of TiIII species. The anal. of the structure of the transition state corresponding to the reduction process (the addition of the hydride to the carbonyl system), provides an interesting insight on the enantioselectivity that characterizes this reaction.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane, is researched, Molecular C19H18N2O2, CAS is 132098-59-0, about Enantioselective Mukaiyama-Michael reactions of 2-carbomethoxycyclopentenone catalyzed by chiral bis(oxazoline)-Cu(II) complexes, the main research direction is carbomethoxycyclopentenone stereoselective Mukaiyama Michael alkoxysilyloxypropene; copper bisoxazoline catalyst stereoselective Mukaiyama Michael.Recommanded Product: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane.

The conjugate addition of propionate silyl ketene acetal to 2-(carbomethoxy)cyclopentenone is promoted by bis(oxazoline)-Cu(II) complexes with high diastereoselectivity and good enantiomeric excesses. The absolute configuration of the product can be controlled by varying the copper counterion. A catalytic version of the reaction was developed, which gave a keto acid in 72% d.e. and 63% e.e.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Application In Synthesis of Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane, is researched, Molecular C19H18N2O2, CAS is 132098-59-0, about Energy-resolved collision-induced dissociation cross sections of 2:1 bis-oxazoline copper complexes: nonbonded interactions and nonlinear effects. Author is Zocher, Eva; Dietiker, Rolf; Chen, Peter.

Absolute ligand binding energies are determined for the 2:1 complexes of bis-oxazoline ligands and Cu(I) in the gas phase by the fitting of energy-resolved collision-induced dissociation cross sections. The complexes were chosen for their occurrence in asym. catalysis for which the phenomenon of nonlinear effects is explained by differences in stability for homochiral and hetero-chiral complexes. Pseudo-enantiomeric ligands are used so that mass spectrometric measurements can be employed. The measurements find that the sterically similar, but electronically different, iso-Pr vs. Ph substituents lead to a different stability ordering of the homo- vs. hetero-chiral complexes, which then leads to the prediction of nonlinear effects in asym. catalysis by the complexes with isopropyl-substituted ligands. The origin of the difference in stability order is found in noncovalent interactions between the Ph groups on the ligands, which are poorly described by DFT calculations

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 132098-59-0, is researched, SMILESS is C1(CC2=N[C@@H](C3=CC=CC=C3)CO2)=N[C@@H](C4=CC=CC=C4)CO1, Molecular C19H18N2O2Journal, Article, Research Support, Non-U.S. Gov’t, Journal of the American Chemical Society called Development of Catalytic Asymmetric 1,4-Addition and [3 + 2] Cycloaddition Reactions Using Chiral Calcium Complexes, Author is Tsubogo, Tetsu; Saito, Susumu; Seki, Kazutaka; Yamashita, Yasuhiro; Kobayashi, Shu, the main research direction is calcium bisoxazoline catalyst asym conjugate addition cycloaddition; glycine Schiff base unsaturated carbonyl cycloaddition calcium bisoxazoline catalyst; pyrrolidine glutamic acid derivative stereoselective preparation.Recommanded Product: 132098-59-0.

Catalytic asym. 1,4-addition and [3 + 2] cycloaddition reactions using chiral calcium species prepared from calcium isopropoxide and chiral bisoxazoline ligands have been developed. Glycine Schiff bases reacted with acrylic esters to afford 1,4-addition products, glutamic acid derivatives, in high yields with high enantioselectivities. During the investigation of the 1,4-addition reactions, we unexpectedly found that a [3 + 2] cycloaddition occurred in the reactions with crotonate derivatives, affording substituted pyrrolidine derivatives in high yields with high enantioselectivities. On the basis of this finding, we investigated asym. [3 + 2] cycloadditions, and it was revealed that several kinds of optically active substituted pyrrolidine derivatives containing contiguous stereogenic tertiary and quaternary carbon centers were obtained with high diastereo- and enantioselectivities. In addition, optically active pyrrolidine cores of hepatitis C virus RNA-dependent polymerase inhibitors and potential effective antiviral agents have been synthesized using this [3 + 2] cycloaddition reaction. NMR spectroscopic anal. and observation of nonamplification of enantioselectivity in nonlinear effect experiments suggested that a monomeric calcium species with an anionic ligand was formed as an active catalyst. A stepwise mechanism of the [3 + 2] cycloaddition, consisting of 1,4-addition and successive intramol. Mannich-type reaction was suggested. Furthermore, modification of the Schiff base structure resulted in a modification of the reaction course from a [3 + 2] cycloaddition to a 1,4-addition, affording 3-substituted glutamic acid derivatives with high diastereo- and enantioselectivities.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Singh, R. P. published an article about the compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane( cas:132098-59-0,SMILESS:C1(CC2=N[C@@H](C3=CC=CC=C3)CO2)=N[C@@H](C4=CC=CC=C4)CO1 ).Quality Control of Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:132098-59-0) through the article.

The configurations of chloro, Et and bis-complexes of Mg with C2-chiral bis-oxazolines such as 2,2′-methylenebis[(4S)-4-isopropyl-2-oxazoline] (MBIO), 2,2′-methylenebis[(4S)-4-tert-butyl-2-oxazoline] (MBTO) and 2,2′-methylenebis[(4S)-4-phenyl-2-oxazoline] (MBPO) were studied from spectroscopic studies. The IR and NMR (1H, 13C) data suggested that the bis-oxazoline ligands coordinated Mg (II) through both the N atoms. The mol. weight determination in nitrobenzene indicated the dimeric nature of chloro and ethylmagnesium complexes whereas bis-Mg complexes are monomeric.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane, is researched, Molecular C19H18N2O2, CAS is 132098-59-0, about Mesopore immobilized copper bis(oxazoline) complexes for enantioselective catalysis.Quality Control of Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane.

Supported heterogeneous catalysts were prepared through the tethering of copper bis(oxazoline) complexes to the surfaces of MCM-41 and MCM-48 mesoporous materials. Thus, treatment of (4S,4’S)-2,2′-methylenebis[4,5-dihydro-4-phenyloxazole] with (3-iodopropyl)trimethoxysilane gave the resp. (4S,4’S)-2,2′-[bis[3-(trimethoxysilyl)propyl]methylene]bis[4,5-dihydro-4-phenyloxazole] (not isolated). Copper chloride (CuCl2) or trifluoromethanesulfonic acid copper(2+) salt were added to the latter ligand and the resulting copper complexes were added to zeolite MCM-41 or MCM-48, resp. The zeolite-tethered catalysts were isolated and studied as cyclopropanation catalysts in the reaction of (ethenyl)benzene with diazoacetic acid Et ester.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 132098-59-0, is researched, SMILESS is C1(CC2=N[C@@H](C3=CC=CC=C3)CO2)=N[C@@H](C4=CC=CC=C4)CO1, Molecular C19H18N2O2Journal, Article, Chemical Communications (Cambridge, United Kingdom) called Copper-catalyzed asymmetric alkynylation of cyclic N-sulfonyl ketimines, Author is Ling, Zheng; Singh, Sonia; Xie, Fang; Wu, Liang; Zhang, Wanbin, the main research direction is alkynylation asym cyclic sulfonyl ketimine copper catalyst; benzisothiazole asym preparation alkynylation cyclic sulfonyl ketimine copper catalyst.Recommanded Product: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane.

A Cu-catalyzed asym. alkynylation of cyclic N-sulfonyl ketimines I (R1 = Et, Me, n-Bu, CHMe2, R2 = H, 5-Me, 7-OCF3, 4,6-Me2, etc.) was developed, providing the corresponding chiral α-tertiary amines II (R3 = Ph, 2-ClC6H4, 4-FC6H4, 2-thienyl, etc.) with up to 98% ee. The method tolerates some variations in cyclic N-sulfonyl ketimine and alkyne scope. These products could be used in several transformations, in particular, the products of 6-membered cyclic N-sulfonyl ketimines could be easily converted to linear chiral α-tertiary amines. This asym. alkynylation provides an efficient, gram-scale, low-cost transition-metal catalyzed synthesis of chiral α-tetrasubstituted propargylamines.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane(SMILESS: C1(CC2=N[C@@H](C3=CC=CC=C3)CO2)=N[C@@H](C4=CC=CC=C4)CO1,cas:132098-59-0) is researched.Quality Control of Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane. The article 《Enantioselective Total Synthesis of (-)-Acutumine》 in relation to this compound, is published in Journal of Organic Chemistry. Let’s take a look at the latest research on this compound (cas:132098-59-0).

An account of the total synthesis of the tetracyclic alkaloid (-)-acutumine (I) is presented. A first-generation approach to the spirocyclic subunit was unsuccessful as a result of incorrect regioselectivity in a radical cyclization. However, this work spawned a second-generation strategy in which the spirocycle was fashioned via a radical-polar crossover reaction. This process merged an intramol. radical conjugate addition with an enolate hydroxylation and created two stereocenters with excellent diastereoselectivity. The reaction was promoted by irradiation with a sunlamp, and a ditin reagent was required for aryl radical formation. These facts suggest that the substrate may function as a sensitizer, thereby facilitating homolytic cleavage of the ditin reagent. The propellane motif of the target was then installed via annulation of a pyrrolidine ring onto the spirocycle. The sequence of reactions used included a phenolic oxidation, an asym. ketone allylation mediated by Nakamura’s chiral allylzinc reagent, an anionic oxy-Cope rearrangement, a one-pot ozonolysis-reductive amination, and a Lewis acid promoted cyclization of an amine onto an α,β-unsaturated di-Me ketal. Further studies of the asym. ketone allylation demonstrated the ability of the Nakamura reagent to function well in a mismatched situation. A TiCl4-catalyzed regioselective Me enol etherification of a 1,3-diketone completed the synthesis.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Singh, R. P. researched the compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane( cas:132098-59-0 ).Name: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane.They published the article 《Syntheses and spectral studies of zinc(II) complexes with C2-chiral bis-oxazolines》 about this compound( cas:132098-59-0 ) in Bulletin de la Societe Chimique de France. Keywords: zinc benzenethiolate chiral oxazoline complex preparation. We’ll tell you more about this compound (cas:132098-59-0).

Zn(II) complexes with C2-chiral bis-oxazoline ligands ClZnL, (PhS)ZnL and (PhS)2ZnLH (LH = 2,2′-methylenebis[(4S)-4-isopropyl-2-oxazoline] (MBIOH), 2,2′-methylenebis[(4S)-4-tert-butyl-2-oxazoline] (MBTOH) and 2,2′-methylenebis[(4S)-4-phenyl-2-oxazoline] (MBPOH)) were described. Studies of the complexes by IR, UV and NMR spectra indicated that the ligands act as bidentates coordinating to Zn(II) with both N atoms. ClZnL and (PhS)ZnL complexes were dimeric whereas (PhS)2ZnLH complexes were monomeric in benzene as found cryoscopically.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles