Intramolecular carbene and nitrene insertions at C-2 of diacetone-d-glucose

Berndt, Daniel; Norris, Peter

doi:10.1016/s0040-4039(02)00698-6

Cited by 20 publications

(14 citation statements)

References 11 publications

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“…In a few cases suitable metal catalysts have been found, although metal–nitrene complexes are not necessarily formed because these species undergo intermolecular reactions to form azoarenes 344. An example of an intramolecular insertion of an acyl azide is the functionalization of furanose derivatives 349 (Scheme ) 346. The newly formed rings are mostly five‐ or six‐membered, of which the smaller rings are formed more readily.…”

Section: Reactions Of Organic Azidesmentioning

confidence: 99%

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

et al. 2005

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Since the discovery of organic azides by Peter Griess more than 140 years ago, numerous syntheses of these energy-rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. In this Review, the fundamental characteristics of azide chemistry and current developments are presented. The focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles. Further reactions such as the aza-Wittig reaction, the Sundberg rearrangement, the Staudinger ligation, the Boyer and Boyer-Aubé rearrangements, the Curtius rearrangement, the Schmidt rearrangement, and the Hemetsberger rearrangement bear witness to the versatility of modern azide chemistry.

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Section: Reactions Of Organic Azidesmentioning

confidence: 99%

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

et al. 2005

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“…In einigen Fällen konnten geeignete Metall‐Katalysatoren gefunden werden, wobei nicht zwingend Metall‐Nitren‐Komplexe gebildet werden, denn diese reagieren intermolekular unter Bildung von Azoarenen 344. Ein Beispiel für eine intramolekulare Insertion unter Verwendung von Acylaziden ist die Funktionalisierung von Furanose‐Derivaten ( 349 ; Schema ) 346. Der neugebildete Ring ist im Allgemeinen fünf‐ oder sechsgliedrig, wobei die kleineren Ringe meist leichter gebildet werden.…”

Section: Reaktionen Organischer Azideunclassified

Organische Azide – explodierende Vielfalt bei einer einzigartigen Substanzklasse

et al. 2005

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Seit der Entdeckung der organischen Azide vor über einhundertvierzig Jahren durch Peter Grieß wurde eine Reihe von Synthesen für diese energiereichen Moleküle entwickelt. In letzter Zeit haben sich völlig neue Perspektiven durch Anwendungen in der Peptidchemie, der kombinatorischen Chemie und der Heterocyclensynthese ergeben. Auf dem interdisziplinären Gebiet zwischen Chemie, Biologie, Medizin und Materialwissenschaften nehmen organische Azide inzwischen einen wichtigen Raum ein. In diesem Aufsatz werden die Grundzüge der Azid‐Chemie dargelegt und aktuelle Entwicklungen auf diesem Gebiet beleuchtet. Der Schwerpunkt liegt dabei auf Cycloadditionen (Huisgen‐Reaktion), Aza‐Ylidchemie und der Synthese von Heterocyclen. Weitere Reaktionen wie die Aza‐Wittig‐Reaktion, Sundberg‐Umlagerung, Staudinger‐Ligation, Boyer‐ und Boyer‐Aubé‐Umlagerung, Curtius‐Umlagerung, Schmidt‐Umlagerung sowie die Hemetsberger‐Umlagerung zeugen von der Vielfältigkeit moderner Azid‐Chemie.

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“…The formed γ‐butyrolactones 50 and 51 were obtained in up to 80 % yield and with an exo/endo selectivity better than 98:2. Another early study was performed by Berndt and Norris, who used nitrenes and carbenes tethered through linkers to C3 (Scheme ) . As the model system diacetone‐ d ‐glucose was chosen because the furanose ring is rigid and hence facilitates the nitrene/carbene insertion.…”

Section: C–h Functionalization Of C2–h To C6–hmentioning

confidence: 99%

C–H Functionalization on Carbohydrates

2016

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Functionalization of C-H bonds has received significant attention in organic chemistry during the last decade and it is still a "hot" topic. In particular, C-H modification of natural products has benefitted from this development. Carbohydrates are densely functionalized natural products, and methods for their functionalization are therefore very attractable. This review presents methods from the last five decades and gives an over-

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Intramolecular carbene and nitrene insertions at C-2 of diacetone-d-glucose

Cited by 20 publications

References 11 publications

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

Organische Azide – explodierende Vielfalt bei einer einzigartigen Substanzklasse

C–H Functionalization on Carbohydrates

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