β‐Ketoesters: An Overview and It's Applications via Transesterification

Rao, G. B. Dharma; Bendi, Anjaneyulu; Kaushik, M. P.; Mailavaram, Raghu Prasad

doi:10.1002/slct.202102949

Cited by 8 publications

(3 citation statements)

References 226 publications

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“…We next turned our attention towards β-ketoesters which are fundamental synthons in organic chemistry. (37)(38)(39) Preliminary experiments starting from commercially available methyl ester 4a(X) using stoichiometric catalyst showed that L-Cys can also facilitate this transformation.…”

Section: Extended Scopementioning

confidence: 99%

Organocatalytic hydration of activated alkynes

González-Rodríguez,

González-Granda,

Lavandera

et al. 2024

Preprint

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Hydration reactions consist of the introduction of a molecule of water into a chemical compound. This process is a particularly useful method to allow, for instance, the conversion of alkynes into carbonyls, which are strategic intermediates in the synthesis of a plethora of compounds. Herein we demonstrate that L-cysteine can catalyse the hydration of activated alkynes in a very effective and fully regioselective manner to access β-ketosulfones, amides and esters in aqueous conditions. The mild reaction conditions facilitated the integration with enzyme catalysis to access chiral β-hydroxy sulfones from the corresponding alkynes in a one-pot cascade process in good yields and excellent enantiomeric excess. These findings pave the way towards establishing a general method for metal-free, cost-effective, and more sustainable alkyne hydration processes

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Section: Extended Scopementioning

confidence: 99%

Organocatalytic hydration of activated alkynes

González-Rodríguez,

González-Granda,

Lavandera

et al. 2024

Preprint

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“…Recently, it has gained more attention in synthesizing drugs, polymers, and biologically active compounds. [75]…”

Section: Transesterificationmentioning

confidence: 99%

“…Several commercial and non‐commercial β‐ketoesters were synthesized through transesterification method utilizing alcohols and variety of acetoacetates. Recently, it has gained more attention in synthesizing drugs, polymers, and biologically active compounds [75] …”

Section: Applications Of Samarium(iii) Triflate In Organic Synthesismentioning

confidence: 99%

Samarium(III) Triflate in Organic Synthesis: a Mild and Efficient Catalyst

Dey

Majhi

2023

ChemistrySelect

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Lanthanides have shown great potential in the field of magnetic materials, telecommunications, hard‐disk drives, catalysis, medicine, agriculture, and more. Recently, lanthanide complexes have gained significant attention in cancer diagnosis and therapy because of the multifunctional chemical and magnetic activities of the lanthanide‐ion 4 f electronic configuration. Among lanthanides, samarium metal and its derivatives have been the subject of many applications in organic transformations. Various metal triflates such as Bi(OTf)3, Yb(OTf)3, In(OTf)3, Sc(OTf)3, Er(OTf)3, Ce(OTf)3, Sm(OTf)3, and others play a profound role in developing novel eco‐friendly protocols in organic synthesis with excellent efficiency and selectivity. Among lanthanide triflate, samarium(III) triflate has a remarkable contribution in synthesizing promising organic molecules as it has been shown to be moisture tolerant and a reusable Lewis catalyst under mild conditions. The present review aims to focus on different useful protocols using samarium(III) triflate as an efficient catalyst for the first time elegantly.

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A Boron Scan of Ethyl Acetoacetate Leads to Versatile Building Blocks

Trofimova,

White,

Diaz

et al. 2024

Angewandte Chemie

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Discovered in the 19th century, ethyl acetoacetate has been central to the development of organic chemistry, including its pedagogy and applications. In this study, we present borylated derivatives of this venerable molecule. A boron handle has been installed at either [[EQUATION]]‐ or [[EQUATION]]‐position of acetoacetate by homologation of acyl‐MIDA (N‐methyliminodiacetic acid) boronates with diazoacetates. Either alkyl or boryl groups were found to migrate with regiochemistry being a function of the steric bulk of the diazo species. Boryl [[EQUATION]]‐ketoesters can be further modified into borylated pyrazolones and oximes, thereby expanding the synthetic toolkit and offering opportunities for additional modifications.

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β‐Ketoesters: An Overview and It's Applications via Transesterification

Cited by 8 publications

References 226 publications

Organocatalytic hydration of activated alkynes

Organocatalytic hydration of activated alkynes

Samarium(III) Triflate in Organic Synthesis: a Mild and Efficient Catalyst

A Boron Scan of Ethyl Acetoacetate Leads to Versatile Building Blocks

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