Awesome Chemistry Experiments For (S)-Diphenyl(pyrrolidin-2-yl)methanol

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The invention discloses a chiral MeCBS synthesis process. The chiral diphenyl dried meat amine alcohol and 1.1 – 1.5 equivalent methyl boric acid is added in an isoparaffinic solvent refluxing separating water, after the reaction, lowering the temperature to 30 – 45 C, after filtering, the filtrate is again lowering the temperature to – 20 – 0 C lower, stirring precipitation, filtration and drying to obtain chiral MeCBS, good fluidity as white solid. The process method is simple in operation, to obtain high purity of product, is currently on the market only in the form of solution supply provides more choices. (by machine translation)

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Metal catalyst and ligand design,
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A process for the epoxidation of an alkene, which process comprises reaction of an alkene with an oxidising agent in the presence of a catalyst, characterised in that the catalyst is an amine of formula (I), wherein T represents hydrogen or a moiety of formula (a); R1, R2, R3, R4, R5 and R6 each independently represents hydrogen, optionally substituted alkyl, an optionally substituted aryl group, heterocyclyl or an optionally substituted aralkyl group wherein substituents for the above mentioned groups are selected from up to three of alkyl, aryl, heterocycyl, hydroxy, alkoxy or a group NRsRt wherein R5 and Rt each independently represents hydrogen, alkyl or alkylcarbonyl and R7 represents hydrogen, alkyl, aryl or aralkyl; or T represents a moiety (a) wherein R1 together with R2 represents an optionally substituted alkylene chain comprising 2 to 6 carbon atoms the alkylene chain being optionally interrupted with an oxygen atom or a group NRp wherein Rp is hydrogen or alkyl, and wherein optional substituents for any carbon atom of the alkylene chain are selected from hydroxy, alkoxy, oxo or a group NRsRt wherein Rs and Rt each independently represents hydrogen, alkyl or alkylcarbonyl or substituents on any two adjacent carbon atoms of the chain together with the carbon atoms to which they are attached form an alicyclic, aryl or heterocyclic ring; and R3, R4, R5, R6 and R7 are as defined above. 1

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The symmetrical P-stereogenic bis-phosphoramidite PCP pincer Pd(II) complexes 1 and 2 were easily prepared by a four-component, one-pot phosphorylation/palladation’ procedure via C-H bond activation of the related ligands. In this synthetic procedure, (S)-diphenyl(pyrrolidin-2-yl)methanol was first phosphonated with PCl3 to afford the expected phosphorochloridate adduct, which then reacted in situ with resorcinol or disubstituted resorcinol, followed by treatment with PdCl2. The first examples of the unsymmetrical P-stereogenic phosphoramidite- and imidazoline-containing PCN pincer Pd(II) complex 3 and Ni(II) complex 4 could be obtained in a similar manner by using a chiral imidazoline-containing m-phenol derivative instead of resorcinol as a backbone. 31P NMR of the complexes confirmed the formation of a single diastereoisomer concerning the P-stereogenic center, and its absolute configuration was determined by an X-ray crystal structure determination. Preliminary investigations on the use of these complexes in the asymmetric allylation indicated that the unsymmetrical pincer Pd complex 3 exhibited higher catalytic activity than the related symmetrical ones. On the other hand, the more bulky Pd complex 2 gave better enantioselectivity, especially in the allylation of 4-nitrobenzenesulfonimine (69% ee).

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Novel oxazaborolidines B-C6F5 were synthesized by modified protocol from C6F5B(OMe)2 (in place of usual C6F5B(OH)2) and the corresponding amino alcohols, aiming to know the pi-pi stacking and electron-withdrawing effects of C6F5 group in asymmetric reduction of ketones. Although the results were not simply explained by the expected effects, significant difference was observed in the enantioselectivity between the catalysts with B-C6H5 and B-C6F5.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Awesome and Easy Science Experiments about (S)-Diphenyl(pyrrolidin-2-yl)methanol

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Chiral diamine catalysts 11a?e derived from alpha,alpha-diphenyl prolinol were prepared and successfully applied to the Michael addition of aromatic oximes to alpha,beta-unsaturated aldehydes in mediocre to good yields (up to 78%) and good to high enantioselectivities (up to 93% ee).

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Top Picks: new discover of (S)-Diphenyl(pyrrolidin-2-yl)methanol

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RhCl(PPh3)3-catalyzed [4+2] intramolecular cycloaddition of optically active axially chiral allene-dienes afforded cis-fused [3.4.0]-bicyclic products with three chiral centers in good yields with an excellent chemo- and diastereoselectivity. A pair of enantiomers of such products was generated highly selectively from both enantiomers of starting allene-dienes, indicating that the axial chirality dictated the absolute configurations of the three in situ generated chiral centers with a very high efficiency of chirality transfer.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Simple exploration of (S)-Diphenyl(pyrrolidin-2-yl)methanol

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Two series of new chiral ligands, squaric acid aminoalcohols and C2-symmetric squaric acid diaminoalcohols have been synthesized. The chiral oxazaborolidines formed in situ from these ligands have been used in the enantioselective borane reduction of prochiral ketones and diketones to afford alcohol products with up to 99% enantiomeric excesses. The structures of the ligands have an obvious effect on the ee of the resulting alcohols.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Go organic! N-Heterocyclic carbene (NHC) 1,3-diisopropyl-4,5- dimethylimidazol-2-ylidene (IiPr) has been found to be an efficient and selective catalyst for the dehydrogenative coupling of a wide range of silanes and hydroxyl groups to form Si-O bonds under mild and solvent-free conditions (see scheme). Mechanistic studies indicated that the activation of hydroxyl groups by the NHC is the most plausible initial step for the process. Copyright

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Some scientific research about (S)-Diphenyl(pyrrolidin-2-yl)methanol

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Optically active aluminum complexes such as Schiff base, binuclear beta-ketoiminate, and bisprolinol complexes were found to promote asymmetric alternating copolymerizations of carbon dioxide and cyclohexene oxide. The aluminum Schiff base complexes-tetraethylammonium acetate afforded isotactic poly(cyclohexene carbonate)s with low enantioselectivities. Lewis bases having two coordinating sites were utilized to enhance activity and selectivity based on the binuclear structure of the aluminum beta-ketoiminate clarified by X-ray crystallography. [2gAlMe]2-bulky bisimidazole produced the alternating copolymer with high enantioselectivity (62% ee). The polymerization is considered to preferentially proceed at more crowded, enantioselective site owing to coordination of bulky Lewis bases to aluminums in less enantioselective sites. 32AlMe-2-picoline also exhibited a high enantioselectivity (67% ee). Methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) was applied to perform faster and more enantioselective copolymerizations at low temperature (82% ee). The asymmetric copolymerizations were found to be significantly dependent on size of epoxide, temperature, and kind/amount of activators.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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A novel method for organocatalytic oxidation through oxidative enamine catalysis was developed with excellent compatibility for the direct syntheses of enals from simple saturated alcohols. By using this amine-catalyzed IBX-oxidation, a wide range of aromatic and aliphatic substituted enals were successfully generated in high yields and exclusively stereoselective E-geometry. Moreover, varying the solvents and/or the loading amounts of IBX allowed for the selective oxidation of alcohols and aldehydes. Importantly, the homologous application of this method provided a selective and efficient way of preparing various highly sensitive conjugated polyene frameworks, which are enriched in natural products.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI