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Publications (33)
A new boric agent with bridged structure, boric acid D, was first synthesized and used as an excellent chiral derivative agent for highly efficient enantiodiscrimination of various diols.
A convenient, safe, and effective synthetic protocol for the synthesis of chiral β-homoglutamic acid was described. The strategy started from 3-cyclohexenecarboxylic acid, followed by three steps classic reaction including Curtius Rearrangement, oxidative cleavage of alkene, and debenzylation by catalytic hydrogenation. The chiral β-homoglutamic ac...
A simple chiral binuclear titanium complex ((S)-Ti2L3Na4) was first prepared and served as an excellent chiral sensor for discriminating a variety of chiral ammoniums by 1H NMR. In the presence of trifluoroacetic acid, the in-situ-generated ammoniums of varied amines can be effectively resolved by (S)-Ti2L3Na4. The different binding forces between...
An axially chiral binuclear μ-hydroxo Pd complex (BPHP) first served as an excellent chiral sensor for discriminating a variety of analytes including amino alcohol, amino amide, amino acid, mandelic acid, diol, diamine and monoamine by ³¹P{¹H} NMR. A detailed recognition mechanism was proposed based on single crystal and mass spectrum of Pd-complex...
In this work, a novel method for assigning the absolute configuration of a chiral primary amine has been developed based on the experimental and DFT-calculated ¹⁹F NMR chemical shift differences of its derived two fluorinated amides by reacting with two enantiomers of a chiral derivatizing agent FPP (α-fluorinated phenylacetic phenylselenoester) se...
A novel chiral octahedral rhodium complex containing fluorine has been developed to be an excellent chiral sensor for a variety of amines including diamines, monoamines, amino alcohols and amino acids,...
A simple strategy for configurational assignments of α-amino acids has been developed by comparison of the proton NMR chemical shift values of α-Hs of N-phthaloyl protected α-amino acids in the presence of (R)-CSA 1 and (S)-CSA 1 respectively. Highly resolved NMR spectra can be obtained directly on mixed solution of the CSAs with N-phthaloyl protec...
An approach to chiral quaternary 3-aminooxindoles via Et 2 Zn catalyzed diastereoselective addition of various Grignard reagents to broad isaltin-derived N-tert -butanesulfinyl ketimines promoted by zinc( ii ) chloride.
Bulky anthracenyl esters could be efficiently synthesized from 2-benzylbenzoic acids via a novel three-step tandem reaction containing intramolecular Friedel–Crafts acylation, enolization, and esterification. A mechanism for the tandem reaction is proposed.
A chiral thiophosphoroamide 4 derived from (1R,2R)-1,2-diaminocyclohexane is used as a highly effective chiral sensor for the chiral recognition of varied acids via ion-pairing and hydrogen-bonding interactions using (1)H, (19)F and (31)P NMR.
A simple one-step synthesized bisthiourea has been used as a highly efficient and versatile chiral sensor for rapid chiral discrimination and enantiomeric excess determination of a wide range of chiral compounds containing alcohol, sulfoxide, lactone, epoxide, amino alcohol, amide, β-chiral carboxylic acid and remote chiral carboxylic acid with the...
Using a single chiral phosphoramide-Zn(II) complex as the catalyst, the asymmetric β-H transfer reduction of aromatic α-trifluoromethyl ketones and enantioselective addition of aromatic aldehydes with Et2Zn in one pot were successfully realized, affording the corresponding additive products of secondary alcohols in high yields (up to 99%) with exce...
Chemical sensors are powerful for the fast recognition of chiral compounds. However, the established sensing systems are less effective for chiral tertiary alcohols. The chiral tertiary alcohol group is an important structural unit in natural products and drug molecules, and its enantioselective recognition represents a significant and challenging...
The asymmetric addition reactions between varied nonaromatic aldehydes and diethylzinc catalyzed by chiral phosphoramide L-1 and thiophosphorodiamide L-4 were thoroughly investigated. Both ligands worked very well for alpha-branched aliphatic and alpha-branched alpha,beta-unsaturated aldehydes. For alpha-non-branched aliphatic aldehydes, L-4 behave...
A highly effective (1)H NMR method for determining the absolute configurations of various chiral α-hydroxyl acids and their derivatives has been developed with the use of bisthioureas (R)-CSA 1 and (S)-CSA 1 as chiral solvating agents in the presence of DABCO, giving distinguishable proton signals with up to 0.66 ppm chemical shift nonequivalence....
In this work, we thoroughly investigated the effect of structural differentiation of a series of N, N-disubstituted chiral diamine ligands on the catalytic asymmetric aldol reactions between trifluoromethyl ketones and linear aliphatic ketones for the construction of chiral trifluoromethyl tertiary alcohols. A highly efficient primary-tertiary diam...
In this study, a series of mono- and dialkylated chiral 1,2-amino phosphinamide ligands derived from modular (1R,2R)-diphenylethylenediamine were successfully applied in the chiral 1,2-amino phosphinamide-Zn(II) catalyzed asymmetric Henry reaction between benzaldehyde and nitromethane. Although chiral N-monosubstituted and N, N-disubstituted 1,2-am...
We have developed a series of new chiral thiophosphorodiamide ligands derived from (1R,2R)-(+)-1,2-diphenylethylenediamine, which are the structural relatives of thioureas. An investigation into their catalytic properties in asymmetric additions of diethylzinc to aldehydes has shown that N,N,N',N'-tetra-substituted chiral thiophosphorodiamides can...
We have demonstrated that a validated QSAR (quantitative structure–activity relationship) model can be constructed between sterimol steric parameters of the N-substituents of chiral 1,2-amino-phosphoramide ligands and the enantiomeric ratios of alcohol products produced in the asymmetric additions of diethylzinc to acetophenone, which is powerful f...
A simple chiral bisthiourea has been used as a highly effective and practical chemical solvating agent (CSA) for diverse α-carboxylic acids in the presence of DMAP. Excellent enantiodiscrimination based on well-resolved α-H NMR signals of the enantiomers of carboxylic acids can be obtained without interference from the chiral bisthiourea and DMAP....
New chiral phosphoramide ligands derived from cinchona alkaloids were developed, which react with diethylzinc to form chiral phosphoramide-Zn(II) complexes containing two Lewis bases and one Lewis acid. These trifunctional complexes can serve as highly efficient chiral catalysts for triple activation of enantioselective addition reactions of diethy...
Our investigation has shown that achiral quaternary ammonium salt has a significant synergistic effect on the asymmetric additions of diethylzinc to aldehydes catalyzed by chiral phosphoramide–Zn(II) complex. The addition of 10 mol % NBu4X can dramatically reduce the loading amount of chiral ligand without sacrificing the excellent reactivity and e...
We have developed a new method for the synthesis of enantiomerically pure Betti base. By using trifluoroacetic acid to replace the more traditionally used hydrochloride acid, the hydrolysis procedure used in the classical synthesis of racemic Betti base was carried out under milder conditions with an improved yield (up to 96%), which was followed b...
Using the asymmetric addition reaction of diethylzinc with benzylaldehyde as a model, we have demonstrated that excellent correlations exist between steric reference parameters (Charton and Sterimol values) for appropriate sets of substituents present on chiral 1,2-amino-phosphoramide ligands and the enantiomeric ratios of alcohol products produced...
A series of new camphorsulfonylated ligands derived from chiral 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) and (+)-camphorsulfonic acid were synthesized by a short and simple synthetic sequence, and their enantioselective catalytic activities were assessed in the nucleophilic addition reaction of dialkylzinc reagents to aldehydes in the presence of...
On the basis of the investigation of the combinational effect of quaternary ammonium salts and organic bases, an added-metal-free catalytic system for nucleophilic addition reactions of a variety of Grignard reagents to diverse ketones in THF solvent has been developed to produce tertiary alcohols in good to excellent yields. By using tetrabutylamm...
The mechanism of interaction between bovine serum albumin (BSA) and 2-naphthylamine (2-NA) in aqueous solution was investigated by fluorescence spectroscopy, circular dichroism (CD) spectra, and UV-vis spectroscopy. It was proved from fluorescence spectra that the fluorescence quenching of BSA by 2-NA was a result of the formation of complex betwee...
The asymmetric unit of the title compound, C(36)H(30)O(4), contains two crystallographically independent mol-ecules of similar geometry. In both mol-ecules, the meth-oxy-meth-oxy groups are disordered over two positions with refined site occupancies of 0.613 (3):0.387 (3) and 0.589 (4):0.411 (4). The dihedral angles between the naphthalene planes w...
