Vanadium-Catalyzed Oxidation of tert-Butyl N-Hydroxycarbamate to tert-Butyl Nitrosoformate and Its Diels–Alder Reaction with Simple and Functionalized Dienes

doi:10.1055/S-0032-1317148

Paper

Vanadium-Catalyzed Oxidation of tert-Butyl N-Hydroxycarbamate to tert-Butyl Nitrosoformate and Its Diels–Alder Reaction with Simple and Functionalized Dienes

Published Sep 13, 2012 · Y. Hoshino, Kenzō Suzuki, Kiyoshi Honda

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Abstract

A general and efficient vanadium-catalyzed oxidation of tert-butyl N-hydroxycarbamate to tert-butyl nitrosoformate using alkyl hydroperoxides as terminal oxidants has been developed. The intermediate nitroso compound was trapped by in situ Diels–Alder reaction with simple and functionalized dienes, providing general access to a variety of functionalized 3,6-dihydro-2H-1,2-oxazines.

Study Snapshot

This study developed a general and efficient vanadium-catalyzed oxidation of tert-butyl N-hydroxycarbamate to tert-butyl nitrosoformate, providing access to various functionalized 3,6-dihydro-2H-1,2-oxa

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Vanadium-Catalyzed Oxidation of tert-Butyl N-Hydroxycarbamate to tert-Butyl Nitrosoformate and Its Diels–Alder Reaction with Simple and Functionalized Dienes

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References

Citations

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This study presents a Pd(II)-catalyzed sequential dehydrogenation reaction of free aliphatic acids, enabling the one-step synthesis of diverse E,E-1,3-dienes, including the antiasthmatic drug seratrodast.

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The hetero-Diels-Alder reaction between nitroso derivatives and conjugated dienes provides valuable tools for the synthesis of biologically interesting molecules.

Iron complexes of tetramine ligands catalyse allylic hydroxyamination via a nitroso–ene mechanism

Iron complexes of tetramine ligands can promote C-N bond formation via allylic amination of alkenes, with a nitroso-ene mechanism and asymmetric induction not observed.

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Our flow reaction systems provide quantitative yields of nitroso Diels-Alder products with no byproducts and significantly shorter reaction times compared to batch reactions.

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t-Butyl hydroperoxide and metal salts effectively oxidize activated alcohols, α-hydroxylate β-hydroxy ketones, and epoxidate alkenes, among other reactions.

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