Rhodium(I)‐Catalyzed Intermolecular Aza‐[4+3] Cycloaddition of Vinyl Aziridines and Dienes: Atom‐Economical Synthesis of Enantiomerically Enriched Functionalized Azepines

A new synthetic application of vinyl aziridines as N‐containing three‐atom components in a rhodium‐catalyzed [4+3] cycloaddition reaction is described. The reaction proceeds well with various silyl dienol ethers and vinyl aziridines, and enables the efficient synthesis of highly functionalized azepi...

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Bibliographic Details
Published in:Angewandte Chemie 2017-01, Vol.129 (5), p.1371-1375
Main Authors: Zhu, Chao‐Ze, Feng, Jian‐Jun, Zhang, Junliang
Format: Article
Language:English
Subjects:
[4+3]-Cycloaddition
Absolute configuration
Catalysis
Chemistry
Chirale Azepine
Chiralitätstransfer
Cycloaddition
Diene
Dienes
Enantiomers
Ethers
Inversions
Rhodium
Selectivity
Substrates
Synthesis
Synthesis (chemistry)
Transformations
Vinylaziridine
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Summary:A new synthetic application of vinyl aziridines as N‐containing three‐atom components in a rhodium‐catalyzed [4+3] cycloaddition reaction is described. The reaction proceeds well with various silyl dienol ethers and vinyl aziridines, and enables the efficient synthesis of highly functionalized azepines in an enantioselective manner with net inversion of absolute configuration. The salient features of the transformation include the use of readily available substrates, high selectivity, and mild reaction conditions, as well as the versatile functionalization of the products. Breite Auswahl: Die Titelreaktion, in der Vinylaziridine als eine dreiatomige Aza‐Komponente agieren, liefert hoch funktionalisierte Azepine in enantioselektiver Weise und unter Inversion der Konfiguration (siehe Schema; Si=Silylschutzgruppe). Die Strategie zeichnet sich durch leicht verfügbare Substrate, hohe Selektivität, milde Reaktionsbedingungen, einfache Skalierung und vielseitige Funktionalisierung der Produkte aus.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201609608