Iridium(I)-catalyzed hydrogen peroxide oxidation of hydroxamic acids and hetero Diels–Alder reaction of the acyl nitroso intermediates with cyclopentadiene

Iwasa, Seiji; Fakhruddin, Ahmad; Tsukamoto, Yasuyuki; Kameyama, Masayuki; Nishiyama, Hisao

doi:10.1016/s0040-4039(02)01277-7

Cited by 40 publications

(15 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[35] There are also a number of methods that generate acylnitroso com- pounds 11 from hydroxamic acids 16 through transitionmetal-catalyzed oxidations in which peroxides are used as a stoichiometric oxidant. [36][37][38][39][40][41] A thorough study of metal catalysts that perform this transformation has been reported. [42] Other methods commonly used to prepare acylnitroso species 11 include the oxidation of nitrile oxides 17, [43] cycloreversion from 9,10-dimethylanthracene adducts 19, [44] photochemical cleavage of 1,2,4-oxadiazole-4-oxides 18, [45] and rearrangement of nitrocarbenes generated from diazo compounds 20.…”

Section: Preparation Of Nitrosocarbonyl Compoundsmentioning

confidence: 99%

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

Bodnar¹,

2011

View full text Add to dashboard Cite

Organic transformations that result in the formation of multiple covalent bonds within the same reaction are some of the most powerful tools in synthetic organic chemistry. Nitrosocarbonyl hetero-Diels–Alder (HDA) reactions allow for the simultaneous stereospecific introduction of carbon–nitrogen and carbon–oxygen bonds in one synthetic step, and provide direct access to 3,6-dihydro-1,2-oxazines. This Review describes the development of the nitrosocarbonyl HDA reaction and the utility of the resulting oxazine ring in the synthesis of a variety of important, biologically active molecules.

show abstract

Section: Preparation Of Nitrosocarbonyl Compoundsmentioning

confidence: 99%

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

Bodnar¹,

2011

View full text Add to dashboard Cite

show abstract

“…Among the tested metallic hydrogen peroxide oxidation systems. Ru(pybox-dh)(pydic), [Ir(coe) 2 Cl] 2 , [Ir(cod)Cl] 2 and CuI were found effective and can be successfully employed to generate acylnitroso intermediates from hydroxamic acids (Scheme 10) [5].…”

Section: B Oxidation Of Hydroxamic Acidsmentioning

confidence: 99%

“…In general, acylnitroso species are obtained from the oxidation of hydroxylamine derivatives, using organic and inorganic oxidants. Currently, hydrogen peroxide is successfully used as an oxidant for the generation of acylnitroso intermediates via its hetero-Diels-Alder reactions with transition metal complexes as catalysts [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Acylnitroso Intermediates and Their Synthetic Applications

Iwasa¹,

Fakhruddin²,

Nishiyama³

2005

MROC

Self Cite

View full text Add to dashboard Cite

Acylnitroso intermediates are usually known as super reactive species, always prepared in situ and can be readily trapped via hetero-Diels-Alder reactions with dienes or with olefins via ene reactions, which open a magnificent access to produce a variety of complicated and very demanding organic molecules. Both of these reactions of acylnitroso species have been proved as the key synthetic tool in the total synthesis of natural products. The synthetic methods used to prepare these intermediates as well as their recent synthetic applications to the total synthesis of natural products are briefly described in this minireview.

show abstract

“…[35] Außerdem sind mehrere Methoden bekannt, welche die Acylnitrosoverbindungen 11 durch übergangsmetallkatalysierte Oxidation der Hydroxamsäuren 16 unter Verwendung stöchimetrischer Mengen an Peroxiden als Oxidationsmittel erzeugen. [36][37][38][39][40][41] Eine eingehende Untersuchung von Metallkatalysatoren für diese Art von Transformation wurde beschrieben. [42] Andere gängige Methoden zur Synthese der Acylnitrosospezies 11 sind die Oxidation von Nitriloxiden 17, [43] die Cycloreversion von 9,10-Dimethylanthracen-Addukten 19, [44] die photochemische Spaltung von 1,2,4-Oxadiazol-4-oxiden 18 [45] und die Umlagerung von aus Diazoverbindungen 20 erzeugten Nitrocarbenen.…”

Section: Synthese Von Nitrosocarbonylverbindungenunclassified

Hetero‐Diels‐Alder‐Reaktionen von Nitrosocarbonylverbindungen als nützliches Verfahren in der organischen Synthese

Bodnar¹,

Miller

2011

Angewandte Chemie

View full text Add to dashboard Cite

Organische Transformationen, die in einem einzigen Reaktionsschritt mehrere kovalente Bindungen aufbauen, zählen zu den leistungsfähigsten Verfahren in der organischen Synthese. Hetero‐Diels‐Alder(HDA)‐Reaktionen von Nitrosocarbonylverbindungen ermöglichen die stereospezifische Einführung von Kohlenstoff‐Stickstoff‐ und Kohlenstoff‐Sauerstoff‐Bindungen in einem einzigen Syntheseschritt und bieten einen direkten Zugang zu 3,6‐Dihydro‐1,2‐oxazinen. In diesem Aufsatz werden die Entwicklung der Nitrosocarbonyl‐HDA‐Reaktion und der Nutzen der daraus erhältlichen Oxazinringe bei der Synthese verschiedener wichtiger biologisch aktiver Verbindungen beschrieben.

show abstract

Iridium(I)-catalyzed hydrogen peroxide oxidation of hydroxamic acids and hetero Diels–Alder reaction of the acyl nitroso intermediates with cyclopentadiene

Cited by 40 publications

References 31 publications

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

Synthesis of Acylnitroso Intermediates and Their Synthetic Applications

Hetero‐Diels‐Alder‐Reaktionen von Nitrosocarbonylverbindungen als nützliches Verfahren in der organischen Synthese

Contact Info

Product

Resources

About