Efficient resolution of (±)-trans-2,3-diphenylpiperazine using (1S)-(+)- 10-camphorsulfonic acid and enrichment of enantiomeric purity of non-racemic 2,3-diphenylpiperazine using different achiral acids
نویسندگان
چکیده
Enantiomerically pure (R,R)-(+)-2,3-diphenylpiperazine with 98% ee was obtained by resolution of the corresponding racemic mixture using (1S)-(+)-10-camphorsulfonic acid. The partially resolved enriched sample of (S,S)-(–)-2,3-diphenylpiperazine with 73% ee was purified to obtain samples of 97% ee using different achiral acids via the preparation of either homochiral or heterochiral hydrogen bonded aggregates.
منابع مشابه
A Crystallization-Induced Asymmetric Transformation using Racemic Phenyl Alanine Methyl Ester Derivatives as Versatile Precursors to Prepare Amino Acids
L-Tyrosine and L-Dopa are the precursors in the biological synthesis of amine neurotransmitters. On the other hand, phenylalanine as an aromatic amino acid (AAA) is a precursor in the synthesis of L-Tyrosine and L-Dopa. For some substrates such as amino acids, resolution by the formation of diastereomers offers an attractive alternative. Among different methods in this case, crystallization-ind...
متن کاملThe preparation of quinoxaline and 2,3-dihydropyrazine derivatives using selectfluor as an efficient and reusable catalyst
Selectfluor [1-(chloro methyl) -4-flouro -1,4-di azonia bicyclo[2,2,2] octane bis (tetraflouro-borate)] catalyzed the preparation of quinoxaline and 2,3-dihydo pyrazine derivatives through one -pot condensation of 1,2-di amines with 1,2-di carbonyls in solvent and under solvent- free conditions. This catalyst is commercially available, inexpensive, reusable, stable to air and moisture, and rela...
متن کاملChemoenzymatic Synthesis of trans-β-Aryl-δ-hydroxy-γ-lactones and Enzymatic Kinetic Resolution of Their Racemic Mixtures.
Two novel and convenient routes to obtain enantiomerically enriched trans-β-aryl-δ-hydroxy-γ-lactones 5a-d with potential antifeedant and anticancer activity were developed. In the first method starting from corresponding enantiomers of γ,δ-unsaturated esters 4a-d derived from enzymatically resolved allyl alcohols 1a-d, both enantiomers of hydroxylactones 5a-d were synthesized with high enantio...
متن کاملEfficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones using nano-sized protonated ZSM–5 as a biodegradable and reusable solid acid catalyst
Nano-sized protonated ZSM–5 ( H-ZSM-5nanozeolite) was successfully synthesized by the hydrothermal method using the bagasse ash (BGA) as a new silica source. Cultivated BGA in the south of the Caspian Sea (Mazandaran province, Iran) was used for extracting silica powder. H-ZSM-5 was characterized by Fourier transform infrared (FT-IR), X-ray diffraction (XRD), scanning electronic microscopy (SEM...
متن کاملA new method for production of chiral 2-aryl-2-fluoropropanoic acids using an effective kinetic resolution of racemic 2-aryl-2-fluoropropanoic acids.
We report a new method for the preparation of chiral 2-aryl-2-fluoropropanoic acids, including 2-fluoroibuprofen, a fluorinated analogue of non-steroidal anti-inflammatory drugs (NSAIDs), by the kinetic resolution of racemic 2-aryl-2-fluoropropanoic acids using enantioselective esterification. By applying pivalic anhydride (Piv2O) as a coupling agent, bis(α-naphthyl)methanol [(α-Np)2CHOH] as an...
متن کامل