Mild, calcium catalysed Beckmann rearrangements

A mild calcium catalysed Beckmann rearrangement has been realised, which forgoes the more traditional harsh reactions conditions associated with the transformation. The catalyst system is shown to be tolerant towards a wide variety of functional groups relevant to natural product synthesis and medic...

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Veröffentlicht in:Chemical communications (Cambridge, England) Jg. 54; H. 6; S. 654 - 657
Hauptverfasser: Kiely-Collins, H. J., Sechi, I., Brennan, P. E., McLaughlin, M. G.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: CAMBRIDGE Royal Soc Chemistry 16.01.2018
Schlagworte:
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ENANTIOSELECTIVE 1,4-ADDITION
CYCLOADDITION
OXIMES
PRODUCT
KETOXIMES
LACTAMS
DERIVATIVES
CARBINOLS
CHLORIDE
AMIDES
ISSN:1359-7345, 1364-548X, 1364-548X
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Beschreibung
Zusammenfassung:A mild calcium catalysed Beckmann rearrangement has been realised, which forgoes the more traditional harsh reactions conditions associated with the transformation. The catalyst system is shown to be tolerant towards a wide variety of functional groups relevant to natural product synthesis and medicinal chemistry and the synthetic utility of the reaction has also been investigated. A preliminary mechanistic investigation was performed to understand the nature of the incoming nucleophile and a possible reaction pathway is described.
Bibliographie:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/c7cc09491d