Synthesis of enantiopure β-amino alcohols via AKR/ARO of epoxides using recyclable macrocyclic Cr(III) salen complexes

Kureshy, Rukhsana I.; Prathap, K. Jeya; Kumar, Manish; Bera, Prasanta Kumar; Khan, Noor‐ul H.; Abdi, Sayed H. R.; Bajaj, Hari C.

doi:10.1016/j.tet.2011.08.077

Cited by 37 publications

(10 citation statements)

References 60 publications

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“…bis(3-tert-butyl-2-hydroxybenzaldehyde) were synthesized by our reported procedure. 58,60 N-Tosylimines were synthesized by the reported method. 61,62 All the solvents were dried by standard procedures, distilled and stored under nitrogen.…”

Section: Discussionmentioning

confidence: 99%

Chiral Cu(ii)-amino alcohol based complexes for asymmetric aza-Henry reaction of N-Ts imines

Choudhary

Das

Kureshy

et al. 2014

Catal. Sci. Technol.

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A series of chiral dimeric ligands 1A-C, 2A-B, 3A-B and 4A derived from (S)/(R) 1,1′-bi(2-naphthol)-bis-aldehyde/piperazine-bis-aldehyde and various aminoalcohols viz., (1R,2S)-(−)-2-aminodiphenylethanol, (1S,2R)-(−)-2-aminodiphenylethanol, (1R,2S)-1-amino-2,3-dihydro-1H-inden-2-ol and (R)-valinol were synthesized. In situ generated complexes 1A-C-, 2A-B-, 3A-B-, 4A-Cu(II)/Cu(I) of dimeric chiral ligands with different copper salts were used as catalysts for the asymmetric aza-Henry reaction of a variety of N-tosylimines as substrates with different nitroalkanes at RT to afford good yields of aza-Henry products (80% with respect to the imines) with excellent enantioselectivity (ee > 99%) in 24 h with nitromethane and high syn selective products with excellent enantioselectivity with nitroethane. The dimeric chiral Cu(II)complex 1A-Cu(II) retained its performance at the gram level and was expediently recycled for a number of times. The enantio-pure aza-Henry product was further used for the synthesis of (S)-levamisole (an anthelminthic agent) in good yield and ee in three steps.

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Section: Discussionmentioning

confidence: 99%

Chiral Cu(ii)-amino alcohol based complexes for asymmetric aza-Henry reaction of N-Ts imines

Choudhary

Das

Kureshy

et al. 2014

Catal. Sci. Technol.

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“…3-tert-butyl-salicylaldehyde (A) and chloromethylsalicylaldehyde (B), dialdehyde (C) and macrocyclic chiral salen ligands (S-1 0 and R-1 0 ) were synthesized by our earlier reported method. 46 Elemental analysis of complexes was done on a CHNS Analyzer, Perkin Elmer model 2400 (United State of America). Proton nuclear magnetic resonance ( 1 H NMR) spectra were obtained with a Bruker F113V spectrometer (made in Switzerland) (200 MHz) and are referenced internally with trimethylsilane.…”

Section: Experimental Section Materials and Methodsmentioning

confidence: 99%

DNA Binding, Antioxidant Activity, and DNA Damage Protection of Chiral Macrocyclic Mn(III) Salen Complexes

et al. 2012

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We are reporting the synthesis, characterization, and calf thymus DNA binding studies of novel chiral macrocyclic Mn(III) salen complexes S-1, R-1, S-2, and R-2. These chiral complexes showed ability to bind with DNA, where complex S-1 exhibits the highest DNA binding constant 1.20 × 10(6) M(-1). All the compounds were screened for superoxide and hydroxyl radical scavenging activities; among them, complex S-1 exhibited significant activity with IC(50) 1.36 and 2.37 μM, respectively. Further, comet assay was used to evaluate the DNA damage protection in white blood cells against the reactive oxygen species wherein complex S-1 was found effective in protecting the hydroxyl radicals mediated plasmid and white blood cells DNA damage.

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“…The asymmetric aminolysis of meso-stilbene catalyzed by Cr-salen complex 1 (Scheme 4). Kureshy and coworkers [55,56] investigated several different approaches to achieve the enantioselective synthesis of vicinal amino alcohols by the ARO of meso-epoxides. One such approach is the use of in situ generated monomeric and polymeric Ti(IV)salen complexes from ligands 32 and 33 (Scheme 9) [55].…”

Section: With Anilines Amines and Carbamatesmentioning

confidence: 99%

“…The same group also synthesized and evaluated a series of enantiopure macrocyclic Cr-salen complexes with different counter ions [56]. After the screening of different reaction conditions, optimal results were obtained for reactions performed in CH 2 Cl 2 /MeOH (9:1 v/v) with 0.5 mol% catalyst loading using catalyst 34 (Figure 14).…”

Section: With Anilines Amines and Carbamatesmentioning

confidence: 99%

Asymmetric Ring-Opening of Epoxides Catalyzed by Metal–Salen Complexes

Lidskog

Wärnmark

2020

Catalysts

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The asymmetric ring-opening of epoxides is an important reaction in organic synthesis, since it allows for the enantioselective installation of two vicinal functional groups with specific stereochemistry within one step from a highly available starting material. An effective class of catalysts for the asymmetric ring-opening of epoxides is metal–salen complexes. This review summarizes the development of metal–salen catalyzed enantioselective desymmetrization of meso-epoxides and kinetic resolution of epoxides with various nucleophiles, including the design and application of both homogeneous- and heterogeneous epoxide-opening catalysts as well as multi-metallic covalent and supramolecular catalytic systems.

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Synthesis of enantiopure β-amino alcohols via AKR/ARO of epoxides using recyclable macrocyclic Cr(III) salen complexes

Cited by 37 publications

References 60 publications

Chiral Cu(ii)-amino alcohol based complexes for asymmetric aza-Henry reaction of N-Ts imines

Chiral Cu(ii)-amino alcohol based complexes for asymmetric aza-Henry reaction of N-Ts imines

DNA Binding, Antioxidant Activity, and DNA Damage Protection of Chiral Macrocyclic Mn(III) Salen Complexes

Asymmetric Ring-Opening of Epoxides Catalyzed by Metal–Salen Complexes

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