Synthesis of Chiral 3,3ʹ-Disubstituted (S)-BINOL Derivatives via the Kumada and Suzuki Coupling and Their
Antibacterial Activity

Ankireddy, Ashok Reddy; Paidikondala, Kalyani; Syed, Rabbani; Gundla, Rambabu; Reddy, Ch. Venkata Ramana; Ganapathi, T.

doi:10.1134/s1070363220080198

Cited by 3 publications

(1 citation statement)

References 26 publications

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“…These compounds were used in combination with BH 3 ·THF to promote the asymmetric Diels–Alder reactions. ( R )- or ( S )- 133 were also used to prepare other BINOL-based compounds for various applications. − …”

Section: Ortho-lithiation At 3-positionmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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1,1′-Bi-2-naphthol (BINOL) has been extensively used as the chirality source in the fields of molecular recognition, asymmetric synthesis, and materials science. The direct electrophilic substitution at the aromatic rings of the optically active BINOL has been developed as one of the most convenient strategies to structurally modify BINOL for diverse applications. High regioselectivity has been achieved for the reaction of BINOL with electrophiles. Depending upon the reaction conditions and substitution patterns, various functional groups can be introduced to the specific positions, such as the 6-, 5-, 4-, and 3-positions, of BINOL. Ortho-lithiation at the 3-position directed by the functional groups at the 2-position of BINOL have been extensively used to prepare the 3- and 3,3′-substituted BINOLs. The use of transition metal-catalyzed C–H activation has also been explored to functionalize BINOL at the 3-, 4-, 5-, 6-, and 7-positions. These regioselective substitutions of BINOL have allowed the construction of tremendous amount of BINOL derivatives with fascinating structures and properties as reviewed in this article. Examples for the applications of the optically active BINOLs with varying substitutions in asymmetric catalysis, molecular recognition, chiral sensing and materials are also provided.

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Section: Ortho-lithiation At 3-positionmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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Synthesis, Alpha-Glucosidase Inhibition and Antibacterial Activities of the New Chiral (R)-3,3′-Disubstituted BINOL-Phosphates

Konda

Ankireddy²,

Velavalapalli³

et al. 2022

Russ J Gen Chem

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Pd-, Cu-, and Ni-Catalyzed Reactions: A Comprehensive Review of the Efficient Approaches towards the Synthesis of Antibacterial Molecules

Zia,

Khalid,

Rasool

et al. 2024

Pharmaceuticals

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A strong synthetic tool for many naturally occurring chemicals, polymers, and pharmaceutical substances is transition metal-catalyzed synthesis. A serious concern to human health is the emergence of bacterial resistance to a broad spectrum of antibacterial medications. The synthesis of chemical molecules that are potential antibacterial candidates is underway. The main contributions to medicine are found to be effective in transition metal catalysis and heterocyclic chemistry. This review underlines the use of heterocycles and certain effective transition metals (Pd, Cu, and Ni) as catalysts in chemical methods for the synthesis of antibacterial compounds. Pharmaceutical chemists might opt for clinical exploration of these techniques due to their potential.

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Synthesis of Chiral 3,3ʹ-Disubstituted (S)-BINOL Derivatives via the Kumada and Suzuki Coupling and Their Antibacterial Activity

Cited by 3 publications

References 26 publications

Regioselective Substitution of BINOL

Regioselective Substitution of BINOL

Synthesis, Alpha-Glucosidase Inhibition and Antibacterial Activities of the New Chiral (R)-3,3′-Disubstituted BINOL-Phosphates

Pd-, Cu-, and Ni-Catalyzed Reactions: A Comprehensive Review of the Efficient Approaches towards the Synthesis of Antibacterial Molecules

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