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• 5057-98-7 cis-1,2-cyclopentanediol 
• 98-88-4 benzoyl chloride 

Relevant academic research and scientific papers

Desymmetrization of meso diols using enantiopure zinc (II) dimers: Synthesis and chiroptical properties

The one-pot metal templated synthesis of enantiopure binuclear Zn (II) complexes Zn2L1–Zn2L4 were obtained by treating (1R,2R)-diphenylethylenediamine or (1S,2S)-diphenylethylenediamine with 2-hydroxy-5-methyl-1

Binuclear Double-Stranded Helicates and Their Catalytic Applications in Desymmetrization of Mesodiols

The ligand L1 of 4-methyl-2,6-diformylphenol and L2 of 4-tert-butyl-2,6-diformylphenol are synthesized through Schiff base condensation with rac-, (R)-(+), or (S)-(-)-1,1′-binaphthyl-2,2′-diamine (BNDA). As a result, the racemic L1rac, L2rac, and enantiopure L1RR, L1SS, L2RR, and L2SS ligands are obtained incorporating Cu(II) and Zn(II) salts by a simple one-pot metal template method. The series of dinuclear complexes of [M2LX2] (here, M = Cu2+, Zn2+ X = acetate ion, chloride ion; L = L1RR, L1SS, L1rac, L2RR, L2SS, L2rac) formulas are obtained in common. Among them, the single crystal X-ray structures for [Zn2L1rac(OAc)2] and [Zn2L1SSCl2] complexes are obtained. The detailed crystal structure and the chiroptical studies performed on these complexes dictates a self-sorting behavior in their self-assembly process and illustrate a chirality transfer from the ligand to the metal center on the complexes. The enantiopure dinuclear complexes [M2LRRX2] and [M2LSSX2] generate enantiopure λλ and ΔΔ isomers, respectively, but the racemic complexes produce only homochiral λλ and ΔΔ assemblies. The detailed studies based on UFLC (Ultra Fast Liquid Chromatography), CD, and single crystal X-ray structure together show the absence of heterochiral λΔ mesocate. All these complexes are adapted as catalysts for desymmetrization of various mesodiols, and the enantiopure complexes are found to give efficient enantioselectivity in desymmetrization of mesodiols with benzoyl chloride to monobenzoylated ester providing 98% yield and 92% ee.

Use of copper(II)/diamine catalysts in the desymmetrisation of?meso-diols and asymmetric Henry reactions: comparison of?(?)-sparteine and (+)-sparteine surrogates

Four new copper(II)/diamine complexes comprising some (+)-sparteine surrogates and a cyclohexane-derived diamine were prepared and evaluated as chiral catalysts in desymmetrisation of meso-diols and asymmetric Henry reactions. Mono-benzoylation reactions generated two products with high enantioselectivity (90:10 to 97:3 er). Asymmetric Henry reactions gave nitro alcohols in 90:10 to 98:2 er. Notably, the sense of induction with the (+)-sparteine surrogates was opposite to that obtained using the copper(II)/(?)-sparteine complex. One of the nitro alcohol products was utilised in a concise synthesis of a chiral morpholine.

Truncated Cinchona alkaloids as catalysts in enantioselective monobenzoylation of meso-1,2-diols

Readily synthesised quincorine and quincoridine derived chiral diamines efficiently catalyse the asymmetric monobenzoylation of cyclic and acyclic meso-1,2-diols. The Royal Society of Chemistry.

Design and synthesis of novel C2-symmetric chiral piperazines and an application to asymmetric acylation of σ-symmetric 1,2-diols

(Chemical Equation Presented) A novel alicyclic chiral C 2-symmetric piperazine, (S,S)-7, is designed and synthesized from L-proline. Benzoylation of a series of cyclic and acyclic meso-1,2-diols with a catalytic amount of (S,S)-7 and CuCl2 provided optically active monobenzoates with high enantioselectivity.

Chiral boron-bridged bisoxazolines: Readily available anionic ligands for asymmetric catalysis

Asymmetric cyclopropanation and monobenzoylation reactions of mesa diols employing borabox catalysts 1 (M = Cu) result in high enantioselectivities. The borabox ligands are anionic analogues of the bisoxazolines 2 and are readily prepared by lithiation of

Asymmetric desymmetrization of meso-1,2-diols by phosphinite derivatives of cinchona alkaloids

An effective catalyst for the asymmetric monobenzoylation of meso-1, 2-diols was designed - the phosphinite derivative of cinchonine (see formula). In the presence of 30 mol % of this catalyst the monobenzoylated products were obtained with high yields an