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The ability of chiral anions, for example bis[1,1?-bi-2-naphtholato]borate, to induce asymmetry in the reactions of prochiral cations was investigated. Ion-pairing of a borate anion with an aziridinium ion was demonstrated by NMR spectroscopy. The addition of N-methyl indole to an iminium ion (benzylidenedimethylammonium) and the ring-opening of an aziridinium ion (1,2-diphenyl-3-azonia-spiro[2.4]heptane) with benzylamine were studied. Low, but significant, (<15%) enantioselectivities were induced in the formation of the diamine benzyl-(1?,2?-diphenyl-2-pyrrolidin-1-yl-ethyl)-amine. The counterion of the additive was found to have a remarkable effect on the yield and the sense of enantioselectivity of these reactions. Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.HPLC of Formula: C20H14O2, you can also check out more blogs about18531-94-7

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The development of small organic molecules with intense and switchable circularly polarized luminescence (CPL) is currently attracting great interest due to their promising applications in chiroptical devices and sensors. In this paper, CPL-active BF2-bridged azaanthracene dimers (BA1 and BA2) were facilely synthesized by incorporating boron difluoride unit to the binaphthalene. BA1 and BA2 show moderate CPL in diluted solutions, however, BA2 exhibited aggregation-amplified red CPL with large dissymmetry factor up to 1.6×10?2. Moreover, acid-/base-triggered CPL switch off/on were also realized via disaggregation/aggregation of BA2 in tetrahydrofuran (THF)/water binary solvents.

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A protocol was developed for the solution-phase synthesis of multigram amounts of two 9-fluorenylmethoxycarbonyl (Fmoc)-protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution-phase-synthesized tetraproline CSPs with that prepared by stepwise solid-phase synthesis revealed that all three had similar chromatographic performance for resolving 53 model analytes. This suggests that the solution-phase synthesis of oligoprolines, which allows for the specific benefits of good batch reproducibility, selector homogeneity, and possibly low cost, is a feasible alternative to the solid-phase synthesis of oligoproline CSPs. Copyright

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A method of synthesizing an optically active cyclic methionine analogue, 3-aminotetrahydrothiophene-3-carboxylic acid (At5c), is described. A Bucherer-Bergs reaction of 4,5-dihydro-3(2H)-thiophenone and the subsequent alkaline hydrolysis of a hydantoin, followed by Cbz protection of the amine, afforded racemic Cbz-At5c (±)-3 in excellent yield. Diastereomeric esters derived from Cbz-At5c (±)-3 and (R)-BINOL could be separated by column chromatography to give both diastereomers with >99% de. X-ray crystallographic analysis revealed the absolute configuration of the synthesized amino acid derived from the less polar diastereomeric ester to be (S).

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Two reactions of phenols with arynes have been developed. If LiTMP base is employed, arynes generated from aryl chlorides react with phenols to form helicenes. o-Arylation of phenols can be achieved by employing tBuONa base in the presence of AgOAc. Direct arylation of binol was achieved leading to the shortest pathway to o,o?-diarylbinols.

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An economic and practical method for preparing enantiomerically pure [1,1?-binaphthalene]-2,2?-diols is reported. Thus, a condensate of threo-(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol and cyclohexanone (CHANP) was used as a resolving agent. A 2:1:1 mixture of racemic [1,1?-binaphthalene]-2,2?-diol, boric acid, and CHANP was refluxed for several hours in THF or MeCN to give a white precipitate of bis((R)-[1,1?-binaphthalene]-2,2?-diol}boric acid CHANP derivative, from the precipitate, and a filtrate separated from the precipitate, (R)- and (S)-[1,1?-binaphthalene]-2,2?-diol of 100% ee were obtained in ca. 65% yield, respectively.

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The invention discloses binaphthol polyether […] chirality molecular pliers and its preparation and use. The polyether […] chirality molecular pliers states the dinaphthol is to chiral binaphthol polyether chains as isolating the base, for to different si teweitewei is mellow […], having a structure of formula (I), formula (II), formula (IV), formula (V) or formula (VI) is shown. The present invention provides the binaphthol polyether […] chirality molecular pliers in identifying chiral molecules in the application of the object, it takes chiral molecule object is D/L – amino acid ester hydrochloride. The invention synthetic molecule the pliers are right D/L – amino acid ester hydrochloride has certain chiral recognition performance, can be used for chiral recognition separating enantiomers. (by machine translation)

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Salen’ along: The iridium(III)-salen complex 1 efficiently catalyzes the title reaction of 2-ethylbenzenesulfonyl azides to give five-membered sultams with high enantioselectivity. Other 2-alkyl-substitued substrates lead to five- and six-membered sultams with high enantioselectivity; the regioselectivity depends upon the substrate and the catalyst used. EDG=electron-donating group. Copyright

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A highly enantioselective iminium salt catalyst has been prepared and tested in the catalytic asymmetric epoxidation of unfunctionalized alkenes, giving up to 95% ee, the highest ee yet reported for iminium salt-catalyzed epoxidation. Catalyst loadings as low as 0.1 mol % may be used.

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The copper-mediated deracemization of the C2-symmetric vaulted biaryl ligands VANOL and VAPOL has been investigated. In the course of the studies that have led to a more reliable procedure for this process, an unprecedented oxidative dimerization of these ligands has been uncovered. The structures of these oxidative dimerization products were elucidated by a series of NMR experiments, and these assignments were supported by other spectroscopic techniques as well as their chemical reactivity. This oxidative dimerization process was not observed for the linear biaryl ligands BANOL and BINOL, although the new deracemization procedure was effective for the generation of BINOL with high optical purity. The (aS)-enantiomers of BINOL, VANOL and VAPOL were accessible with a copper complex of (-)-sparteine, and the (aR)-enantiomeric series were accessible with a copper complex of O’Brien’s diamine. Both (-)-sparteine and O’Brien’s diamine give higher optical purities with VANOL and VAPOL than with BINOL, and this is consistent with the steric congestion present in the matched and mismatched copper complexes of these diamines with the biaryl ligands.

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Metal catalyst and ligand design,
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