Selectivities in the 1,3-dipolar cycloaddition of nitrile oxides to dicyclopentadiene and its derivatives

Namboothiri, Irishi N. N.; Rastogi, Namrata; Ganguly, Bishwajit; Mobin, Shaikh M.; Cojocaru, Miriam

doi:10.1016/j.tet.2003.12.026

Cited by 28 publications

(8 citation statements)

References 93 publications

(21 reference statements)

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“…Immobilized whole cells of B. pallidus in calcium alginate were found to be more resistant to high concentrations of 3‐cyanopyridine and nicotinic acid than those of free cells . Similarly, polyacrylnitrile immobilization of Rhodococcus and A. facilis improved their nitrile hydrolyzing activity during production of acrylic acid and 4‐cyanopentanoic acid ammonium salt correspondingly. The alginate provided some thermal stabilization for enzyme durability as monitored with immobilized cells of P. thermophila and R. rhodococcus J1.…”

Section: Immobilizationmentioning

confidence: 97%

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Nitrile‐converting enzymes: An eco‐friendly tool for industrial biocatalysis

Ramteke

Maurice

Joseph

et al. 2013

Biotech and App Biochem

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Nitriles are organic compounds bearing a − C ≡ N group; they are frequently known to occur naturally in both fauna and flora and are also synthesized chemically. They have wide applicability in the fields of medicine, industry, and environmental monitoring. However, the majority of nitrile compounds are considered to be lethal, mutagenic, and carcinogenic in nature and are known to cause potential health problems such as nausea, bronchial irritation, respiratory distress, convulsions, coma, and skeletal deformities in humans. Nitrile-converting enzymes, which are extracted from microorganisms, are commonly termed nitrilases and have drawn the attention of researchers all over the world to combat the toxicity of nitrile compounds. The present review focuses on the utility of nitrile-converting enzymes, sources, classification, structure, properties, and applications, as well as the future perspective on nitrilases.

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Section: Immobilizationmentioning

confidence: 97%

“…Entrapment in hydrogels such as calcium alginate , barium alginate , pectinate, k‐carrageenan, and polyacrylamide was used for immobilization of nitrile‐converting enzymes . Some of the immobilized preparations showed a marked thermal or chemical stability.…”

Section: Immobilizationmentioning

confidence: 99%

Nitrile‐converting enzymes: An eco‐friendly tool for industrial biocatalysis

Ramteke

Maurice

Joseph

et al. 2013

Biotech and App Biochem

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“…The regioisomer ratio was 80:20 for norbornene 44. However, for 2-substituted-5-norbornenes 43, the regioisomeric ratio was nearly 1:1 (Scheme 20 Namboothiri et al [43] reported nitrile oxide cycloaddition to dicyclopentadiene and its derivatives. The reaction gave exclusively the exo adduct as a 1:1 ratio of regioisomers for dicyclopentadiene 49a and >99:1 for dimethyldicyclopentadiene dicarboxylate 49b.…”

Section: Cycloaddition Of Nitrile Oxides To Alkenesmentioning

confidence: 99%

Recent Advances in Nitrile Oxide Cycloadditions. Synthesis of Isoxazolines

Sibi¹

2011

COS

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Synthesis of novel heterocyclic compounds continues to be an important and challenging task. Isoxazolines are one such class of heterocyclic molecules of significance, since they are frequently found in many compounds that show significant biological activity. They are also of importance since they can be easily transformed into important functional groups. Nitrile oxide cycloaddition with carbon dipolarophiles represents an easy route to the synthesis of these molecules. Research groups over the past decades have established novel protocols and methods for the synthesis of isoxazolines via dipolar cycloaddition. This review will highlight the success that has been achieved in this field since 2000.

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“…However, better diastereoselectivity (3.2:1) 40 was obtained when the addition was performed under Lewis acid catalyzed (BOX, Mg(OTf) 2 ) conditions. 41 Similarly, 1,3-dipolar cycloaddition of 12a with benzonitrile oxide, generated in situ from benzaldoxime, 42 …”

Section: A-b 11imentioning

confidence: 99%