Huayin Huang

Publications (3)11.25 Total impact

• Article: Constructing a Quantitative Correlation between N-Substituent sizes of Chiral Ligands and Enantioselectivities in Asymmetric Addition Reactions of Diethylzinc with Benzaldehyde.

  Huayin Huang, Hua Zong, Guangling Bian, Ling Song
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  ABSTRACT: 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 in this process.
  The Journal of Organic Chemistry 11/2012; · 4.45 Impact Factor
• Article: The Syntheses of new Camphorsulfonylated Ligands Derived from 2-Amino-2'-Hydroxy-1,1'-Binaphthyl and Their Enantioselectivities in the Addition of Dialkylzinc Reagents to Aldehydes.

  Guangling Bian, Huayin Huang, Hua Zong, Ling Song
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  ABSTRACT: 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 titanium tetraisopropoxide. The most efficient ligand, N-hydroxycamphorsulfonylated (S)-NOBIN, gave (S)-addition products with good yields and up to 87% of ee value. The (1) H nuclear magnetic resonance (NMR) and (13) C NMR results of the titanium titration experiments on this ligand indicate that the most likely catalytic reactive species involved in this catalytic asymmetric addition is a bimetallic titanium complex. A possible catalytic reaction mechanism is proposed. Chirality 24:825-832, 2012. © 2012 Wiley Periodicals, Inc.
  Chirality 06/2012; 24(10):825-32. · 2.35 Impact Factor
• Article: Added-metal-free catalytic nucleophilic addition of Grignard reagents to ketones.

  Hua Zong, Huayin Huang, Junfeng Liu, Guangling Bian, Ling Song
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  ABSTRACT: 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 tetrabutylammonium chloride (NBu(4)Cl) as a catalyst and diglyme (DGDE) as an additive, this system strongly enhances the efficiency of addition at the expense of enolization and reduction. NBu(4)Cl should help to shift the Schlenk equilibrium of Grignard reagents to the side of dimeric Grignard reagents to favor the additions of Grignard reagents to ketones via a favored six-membered transition state to form the desired tertiary alcohols, and DGDE should increase the nucleophilic reactivities of Grignard reagents by coordination. This catalytic system has been applied in the efficient synthesis of Citalopram, an effective U.S. FDA-approved antidepressant, and a recyclable version of this catalytic synthesis has also been devised.
  The Journal of Organic Chemistry 04/2012; 77(10):4645-52. · 4.45 Impact Factor